Alkoxyalkyl-Substituted Cyclic Keto-Enols

ABSTRACT

The invention relates to new alkoxyalkyl-substituted cyclic ketoenols of the formula (I) 
     
       
         
         
             
             
         
       
     
     in which A, B, D, G, W, X, Y and Z have the definitions indicated above,
 
to a number of processes and intermediates for their preparation, and to their use as pesticides and/or herbicides and/or microbicides.
 
     The invention further provides selectively herbicidal, compositions which comprise alkoxyalkyl-substituted cyclic ketoenols on the one hand and a crop plant tolerance promoter compound on the other. 
     The invention further relates to the boosting of the action of crop protection compositions comprising compounds of the formula (I) through the additions of ammonium salts or phosphonium salts and optionally penetration promoters.

The present invention relates to new alkoxyalkyl-substituted cyclicketoenols, to a number of processes for their preparation, and to theiruse as pesticides and/or herbicides and/or microbicides. Also subjectmatter of the invention are selectively herbicidal compositions whichcomprise alkoxyalkyl-substituted cyclic ketoenols on the one hand and acrop plant tolerance promoter compound on the other.

The present invention further relates to the boosting of the action ofcrop protection compositions comprising, in particular,alkoxyalkyl-substituted cyclic ketoenols, through the addition ofammonium salts or phosphonium salts and optionally penetrants, to thecorresponding compositions, to processes for producing them and to theirapplication in crop protection as insecticides and/or acaricides and/orfor preventing unwanted plant growth.

For 3-acylpyrrolidine-2,4-diones pharmaceutical properties have beenpreviously described (S. Suzuki et al. Chem. Pharm. Bull. 15 1120(1967)). Furthermore, N-phenylpyrrolidine-2,4-diones have beensynthesized by R. Schmierer and H. Mildenberger (Liebigs Ann. Chem.1985, 1095). Biological activity of these compounds has not beendescribed.

EP-A-0 262 399 and GB-A-2 266 888 disclose similarly structuredcompounds (3-arylpyrrolidine-2,4-diones) for which, however, noherbicidal, insecticidal or acaricidal action has been disclosed. Knowncompounds with herbicidal, insecticidal or acaricidal action areunsubstituted, bicyclic 3-arylpyrrolidine-2,4-dione derivatives(EP-A-355 599, EP-A-415 211 and JP-A-12-053 670) and also substitutedmonocyclic 3-arylpyrrolidine-2,4-dione derivatives (EP-A-377 893 andEP-A-442 077).

Additionally known are polycyclic 3-arylpyrrolidine-2,4-dionederivatives (EP-A-442 073) and also 1H-arylpyrrolidinedione derivatives(EP-A-456 063, EP-A-521 334, EP-A-596 298, EP-A-613 884, EP-A-613 885,WO 94/01 997, WO 95/26 954, WO 95/20 572, EP-A-0 668 267, WO 96/25 395,WO 96/35 664, WO 97/01 535, WO 97/02 243, WO 97/36 868, WO 97/43275, WO98/05638, WO 98/06721, WO 98/25928, WO 99/24437, WO 99/43649, WO99/48869 and WO 99/55673, WO 01/17972, WO 01/23354, WO 01/74770, WO03/013249, WO 03/062244, WO 2004/007448, WO 2004/024 688, WO 04/065366,WO 04/080962, WO 04/111042, WO 05/044791, WO 05/044796, WO 05/048710, WO05/049596, WO 05/066125, WO 05/092897, WO 06/000355, WO 06/029799, WO06/056281, WO 06/056282, WO 06/089633 and DE-A-05051325). Moreover,ketal-substituted 1-H-arylpyrrolidine-2,4-diones are known from WO99/16748, and (spiro)ketal-substituted N-alkoxyalkoxy-substitutedarylpyrrolidinediones are known from JP-A-14 205 984 and Ito M. et al.,Bioscience, Biotechnology and Biochemistry 67, 1230-1238, (2003).

The herbicidal and/or acaricidal and/or insecticidal activity and/orbreadth of action and/or the plant tolerance of the known compounds,particularly with respect to crop plants, is nevertheless not alwayssufficient.

New compounds of the formula (I) have now been found

in which

-   W represents hydrogen, alkyl, alkenyl, alkynyl, halogen, alkoxy,    alkenyloxy, haloalkyl, haloalkoxy or cyano,-   X represents halogen, alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy,    alkylthio, alkylsulphinyl, alkylsulphonyl, haloalkyl, haloalkoxy,    haloalkenyloxy, nitro or cyano,-   Y and Z independently of one another represent hydrogen, alkyl,    alkenyl, alkynyl, alkoxy, halogen, haloalkyl, haloalkoxy, cyano,    nitro or in each case optionally substituted aryl or hetaryl,    -   with the proviso that one of the radicals, Y or Z, represents in        each case optionally substituted aryl or hetaryl,-   A represents a C₁-C₆-alkanediyl radical,-   B represents hydrogen, alkyl or alkoxyalkyl,-   D represents in each case optionally substituted alkoxy, alkenyloxy,    alkynyloxy, alkoxyalkoxy, phenoxy, hetaryloxy, phenylalkoxy,    hetarylalkoxy and represents optionally substituted, saturated or    unsaturated cycloalkyl interrupted by one or optionally two oxygen    atoms or-   A represents a bond,-   B represents hydrogen or alkyl,-   D represents optionally substituted, saturated or unsaturated    C₅-C₆-cycloalkyl interrupted by one or optionally two oxygen atoms,-   G represents hydrogen (a) or represents one of the groups

-   -   in which    -   E represents a metal ion or an ammonium ion,    -   L represents oxygen or sulphur,    -   M represents oxygen or sulphur,

-   R¹ represents in each case optionally halogen- or cyano-substituted    alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl or polyalkoxyalkyl or    represents in each case optionally halogen-, alkyl- or    alkoxy-substituted cycloalkyl or heterocyclyl or represents in each    case optionally substituted phenyl, phenylalkyl, hetaryl,    phenoxyalkyl or hetaryloxyalkyl,

-   R² represents in each case optionally halogen- or cyano-substituted    alkyl, alkenyl, alkoxyalkyl or polyalkoxyalkyl or represents in each    case optionally substituted cycloalkyl, phenyl or benzyl,

-   R³, R⁴ and R⁵ independently of one another represent in each case    optionally halogen-substituted alkyl, alkoxy, alkylamino,    dialkylamino, alkylthio, alkenylthio or cycloalkylthio or represent    in each case optionally substituted phenyl, benzyl, phenoxy or    phenylthio,

-   R⁶ and R⁷ independently of one another represent hydrogen, represent    in each case optionally halogen- or cyano-substituted alkyl,    cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, represent in each case    optionally substituted phenyl or benzyl, or, together with the N    atom to which they are attached, form a ring system which optionally    contains oxygen or sulphur and is optionally substituted.

The compounds of the formula (I), in dependence inter alia on the natureof the substituents, may be present in the form of optical isomers orisomer mixtures, in different compositions, which if desired may beseparated in a conventional manner. Not only the pure isomers but alsothe isomer mixtures, their preparation and use, and compositionscomprising them are subject matter of the present invention. In the textbelow, however, for the sake of simplicity, reference will always bemade to compounds of the formula (I), although this covers not only thepure compounds but also, where appropriate, mixtures with differentfractions of isomeric compounds.

Including the various definitions (a), (b), (c), (d), (e), (f) and (g)of the group G produces the following primary structures (I-a) to (I-g),

in which

-   A, B, D, E, L, M, W, X, Y, Z, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ possess    the definitions indicated above.

In addition it has been found that the new compounds of the formula (I)are obtained by the processes described below:

-   (A) compounds of the formula (I-a)

-   -   in which    -   A, B, D, W, X, Y and Z have the definitions indicated above    -   are obtained if    -   compounds of the formula (II)

-   -   in which    -   A, B, D, W, X, Y and Z have the definitions indicated above and    -   R⁸ represents alkyl (preferably C₁-C₆-alkyl)    -   are subjected to intramolecular condensation in the presence of        a diluent and in the presence of a base.

Moreover, it has been found

-   (B) that the compounds of the above-shown formula (I-b) in which R¹,    A, B, D, W, X, Y and Z have the definitions indicated above are    obtained if compounds of the above-shown formula (I-a) in which A,    B, D, W, X, Y and Z have the definitions indicated above are    subjected to reaction respectively    -   α) with compounds of the formula (III)

-   -   in which        -   R¹ has the definition indicated above and        -   Hal represents halogen (especially chlorine or bromine) or    -   β) with carboxylic anhydrides of the formula (IV)

R¹—CO—O—CO—R¹  (IV)

-   -   in which        -   R¹ has the definition indicated above,    -   optionally in the presence of a diluent and optionally in the        presence of an acid-binding agent;

-   (C) that the compounds of the above-shown formula (I-c) in which R²,    A, B, D, W, M, X, Y and Z have the definitions indicated above and L    represents oxygen are obtained if compounds of the above-shown    formula (I-a) in which A, B, D, W, X, Y and Z have the definitions    indicated above are subjected to reaction respectively    -   with chloroformic esters or chloroformic thioesters of the        formula (V)

R²-M—CO—Cl  (V)

-   -   in which    -   R² and M have the definitions indicated above,    -   optionally in the presence of a diluent and optionally in the        presence of an acid-binding agent;

-   (D) that compounds of the above-shown formula (I-c) in which R², A,    B, D, W, M, X, Y and Z have the definitions indicated above and L    represents sulphur are obtained if compounds of the above-shown    formula (I-a) in which A, B, D, W, X, Y and Z have the definitions    indicated above are subjected to reaction respectively    -   with chloromonothioformic esters or chlorodithioformic esters of        the formula (VI)

-   -   in which    -   M and R² have the definitions indicated above,    -   optionally in the presence of a diluent and optionally in the        presence of an acid-binding agent;

-   (E) that compounds of the above-shown formula (I-d) in which R³, A,    B, D, W, X, Y and Z have the definitions indicated above are    obtained if compounds of the above-shown formula (I-a) in which A,    B, D, W, X, Y and Z have the definitions indicated above are    subjected to reaction respectively    -   with sulphonyl chlorides of the formula (VII)

R³—SO₂—Cl  (VII)

-   -   in which    -   R³ has the definition indicated above,    -   optionally in the presence of a diluent and optionally in the        presence of an acid-binding agent;

-   (F) that compounds of the above-shown formula (I-e) in which L, R⁴,    R⁵, A, B, D, W, X, Y and Z have the definitions indicated above are    obtained if compounds of the above-shown formula (I-a) in which A,    B, D, W, X, Y and Z have the definitions indicated above are    subjected to reaction respectively    -   with phosphorus compounds of the formula (VII)

-   -   in which    -   L, R⁴ and R⁵ have the definitions indicated above and    -   Hal represents halogen (especially chlorine or bromine),    -   optionally in the presence of a diluent and optionally in the        presence of an acid-binding agent;

-   (G) that compounds of the above-shown formula (I-f) in which E, A,    B, D, W, X, Y and Z have the definitions indicated above are    obtained if compounds of the formula (I-a) in which A, B, D, W, X, Y    and Z have the definitions indicated above are subjected to reaction    respectively    -   with metal compounds or amines of the formulae (IX) or (X)

-   -   in which    -   Me represents a monovalent or divalent metal (preferably an        alkali metal or alkaline earth metal such as lithium, sodium,        potassium, magnesium or calcium),    -   t represents the number 1 or 2 and    -   R¹⁰, R¹¹, R¹² independently of one another represent hydrogen or        alkyl (preferably C₁-C₈-alkyl),    -   optionally in the presence of a diluent;

-   (H) that compounds of the above-shown formula (I-g) in which L, R⁶,    R⁷, A, B, D, W, X, Y and Z have the definitions indicated above are    obtained if compounds of the above-shown formula (I-a) in which A,    B, D, W, X, Y and Z have the definitions indicated above are    subjected to reaction respectively    -   α) with isocyanates or isothiocyanates of the formula (XI)

R⁶—N═C=L  (XI)

-   -   in which    -   R⁶ and L have the definitions indicated above,    -   optionally in the presence of a diluent and optionally in the        presence of a catalyst, or    -   β) with carbamoyl chlorides or thiocarbamoyl chlorides of the        formula (XII)

-   -   -   in which        -   L, R⁶ and R⁷ have the definitions indicated above,        -   optionally in the presence of a diluent and optionally in            the presence of an acid-binding agent;

-   (Iα) that compounds of the above-shown formulae (I-a) to (I-g) in    which A, B, D, G, W, X, Y and Z have the definition indicated above    are obtained if compounds of the formulae (I-a′) to (I-g′) in which    A, B, D, G, W, X and Y have the definition stated above and Z′    preferably represents bromine or iodine

-    and-   (Iβ) that compounds of the above-shown formulae (I-a) to (I-g) in    which A, B, D, G, W, X, Y and Z have the definition indicated above    are obtained if compounds of the formulae (I-a″) to (I-g″) in which    A, B, D, G, W, X and Z have the definition stated above and Y′    preferably represents bromine or iodine

are subjected to coupling with couplable (Het)aryl derivatives, e.g.phenylboronic acids of the formulae (XIXα) and (XIXβ)

or esters thereof in the presence of a solvent, in the presence of acatalyst (e.g. Pd complexes) and in the presence of a base (e.g. sodiumcarbonate, potassium phosphate).

The following compounds of the formula (I-a) have been disclosed in thecontext of the European patent examination proceedings relating toEP-A-835 243 and EP-A-837 847.

In addition it has been found that the new compounds of the formula (I)exhibit good activity as pesticides, preferably as insecticides and/oracaricides and/or fungicides and/or herbicides, and, furthermore, arefrequently very well tolerated by plants, in particular by crop plants.

Surprisingly it has now also been found that certain substituted cyclicketoenols, when employed together with the crop plant tolerance promotercompounds (safeners/antidotes) described later on, are extremely good atpreventing damage to the crop plants and can be used with particularadvantage as broad-spectrum combination products for the selectivecontrol of unwanted plants in crops of utility plants, such as incereals but also in maize, soya and rice, for example.

The invention also provides selective-herbicidal compositions comprisingan effective amount of an active-compound combination comprising ascomponents

-   -   (a′) at least one compound of the formula (I), in which A, B, D,        G, W, X, Y and Z have the definition indicated above and    -   (b′) at least one crop plant tolerance promoter compound from        the following group of compounds:    -   4-dichloroacetyl-1-oxa-4-azaspiro[4.5]decane (AD-67, MON-4660),        1-dichloroacetyl-hexa-hydro-3,3,8a-trimethylpyrrolo[1,2-a]pyrimidin-6(2H)one        (dicyclonon, BAS-145138),        4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine        (benoxacor), 1-methylhexyl 5-chloroquinoline-8-oxyacetate        (cloquintocet-mexyl—cf. also related compounds in EP-A-86750,        EP-A-94349, EP-A-191736, EP-A-492366),        3-(2-chlorobenzyl)-1-(1-methyl-1-phenylethyl)urea (cumyluron),        α-(cyanomethoximino)phenylacetonitrile (cyometrinil),        2,4-dichlorophenoxyacetic acid (2,4-D),        4-(2,4-dichlorophenoxy)butyric acid (2,4-DB),        1-(1-methyl-1-phenylethyl)-3-(4-methylphenyl)urea (daimuron,        dymron), 3,6-dichloro-2-methoxybenzoic acid (dicamba),        S-1-methyl-1-phenylethyl piperidine-1-thiocarboxylate        (dimepiperate),        2,2-dichloro-N-(2-oxo-2-(2-propenylamino)ethyl)-N-(2-propenyl)acetamide        (DKA-24), 2,2-dichloro-N,N-di-2-propenyl-acetamide (dichlormid),        4,6-dichloro-2-phenylpyrimidine (fenclorim), ethyl        1-(2,4-dichlorophenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylate        (fenchlorazole-ethyl—cf. also related compounds in EP-A-174562        and EP-A-346620), phenylmethyl        2-chloro-4-trifluoromethylthiazole-5-carboxylate (flurazole),        4-chloro-N-(1,3-dioxolan-2-ylmethoxy)-α-trifluoroacetophenone        oxime (fluxofenim),        3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyl-oxazolidine        (furilazole, MON-13900), ethyl        4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate        (isoxadifen-ethyl—cf. also related compounds in WO-A-95/07897),        1-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate        (lactidichlor), (4-chloro-o-tolyloxy)acetic acid (MCPA),        2-(4-chloro-o-tolyloxy)propionic acid (mecoprop),        diethyl-1-(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate        (mefenpyr-diethyl—cf. also related compounds in WO-A-91/07874),        2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191),        2-propenyl-1-oxa-4-azaspiro[4.5]decane-4-carbodithioate        (MG-838), 1,8-naphthalic anhydride,        α-(1,3-dioxolan-2-ylmethoximino)phenylacetonitrile        (oxabetrinil),        2,2-dichloro-N-(1,3-dioxolan-2-ylmethyl)-N-(2-propenyl)acetamide        (PPG-1292), 3-dichloroacetyl-2,2-dimethyloxazolidine (R-28725),        3-dichloroacetyl-2,2,5-trimethyloxazolidine (R-29148),        4-(4-chloro-o-tolyl)butyric acid, 4-(4-chlorophenoxy)-butyric        acid, diphenylmethoxyacetic acid, methyl diphenylmethoxyacetate,        ethyl diphenylmethoxyacetate, methyl        1-(2-chlorophenyl)-5-phenyl-1H-pyrazole-3-carboxylate, ethyl        1-(2,4-dichlorophenyl)-5-methyl-1H-pyrazole-3-carboxylate, ethyl        1-(2,4-dichloro-phenyl)-5-isopropyl-1H-pyrazole-3-carboxylate,        ethyl        1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)-1H-pyrazole-3-carboxylate,        ethyl 1-(2,4-dichlorophenyl)-5-phenyl-1H-pyrazole-3-carboxylate        (cf. also related compounds in EP-A-269806 and EP-A-333131),        ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate, ethyl        5-phenyl-2-isoxazoline-3-carboxylate, ethyl        5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (cf.        also related compounds in WO-A-91/08202), 1,3-dimethylbut-1-yl        5-chloroquinoline-8-oxy-acetate, 4-allyloxybutyl        5-chloroquinoline-8-oxyacetate, 1-allyl-oxyprop-2-yl        5-chloroquinoline-8-oxyacetate, methyl        5-chloroquinoxaline-8-oxyacetate, ethyl        5-chloroquinoline-8-oxyacetate, allyl        5-chloroquinoxaline-8-oxyacetate, 2-oxoprop-1-yl        5-chloro-quinoline-8-oxyacetate, diethyl        5-chloroquinoline-8-oxymalonate, diallyl        5-chloroquinoxaline-8-oxymalonate, diethyl        5-chloroquinoline-8-oxymalonate (cf. also related compounds in        EP-A-582198), 4-carboxychroman-4-ylacetic acid (AC-304415, cf.        EP-A-613618), 4-chlorophenoxyacetic acid,        3,3′-dimethyl-4-methoxybenzophenone,        1-bromo-4-chloromethylsulphonylbenzene,        1-[4-(N-2-methoxybenzoylsulphamoyl)-phenyl]-3-methylurea (also        known as        N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)-amino]benzenesulphonamide),        1-[4-(N-2-methoxybenzoylsulphamoyl)phenyl]-3,3-di-methylurea,        1-[4-(N-4,5-dimethylbenzoylsulphamoyl)phenyl]-3-methylurea,        1-[4-(N-naphthylsulphamoyl)phenyl]-3,3-dimethylurea,        N-(2-methoxy-5-methylbenzoyl)-4-(cyclo-propylaminocarbonyl)benzenesulphonamide,    -   and/or one of the following compounds, defined by general        formulae,    -   of the general formula (IIa)

-   -   or of the general formula (IIb)

-   -   or of the formula (IIc)

-   -   where    -   m represents a number 0, 1, 2, 3, 4 or 5,    -   A¹ represents one of the divalent heterocyclic groupings shown        below

-   -   n represents a number 0, 1, 2, 3, 4 or 5,    -   A² represents optionally C₁-C₄-alkyl- and/or        C₁-C₄-alkoxycarbonyl- and/or        C₁-C₄-alkenyloxycarbonyl-substituted alkanediyl having 1 or 2        carbon atoms,    -   R¹⁴ represents hydroxyl, mercapto, amino, C₁-C₆-alkoxy,        C₁-C₆-alkylthio, C₁-C₆-alkyl-amino or di(C₁-C₄-alkyl)amino,    -   R¹⁵ represents hydroxyl, mercapto, amino, C₁-C₇-alkoxy,        C₁-C₆-alkylthio, C₁-C₆-alkenyloxy,        C₁-C₆-alkenyloxy-C₁-C₆-alkoxy, C₁-C₆-alkylamino or        di(C₁-C₄-alkyl)amino,    -   R¹⁶ represents optionally fluorine-, chlorine- and/or        bromine-substituted C₁-C₄-alkyl,    -   R¹⁷ represents hydrogen, in each case optionally fluorine-,        chlorine- and/or bromine-substituted C₁-C₆-alkyl, C₂-C₆-alkenyl        or C₂-C₆-alkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,        dioxolanyl-C₁-C₄-alkyl, furyl, furyl-C₁-C₄-alkyl, thienyl,        thiazolyl, piperidinyl, or optionally fluorine-, chlorine-        and/or bromine- or C₁-C₄-alkyl-substituted phenyl,    -   R¹⁸ represents hydrogen, in each case optionally fluorine-,        chlorine- and/or bromine-substituted C₁-C₆-alkyl, C₂-C₆-alkenyl        or C₂-C₆-alkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,        di-oxolanyl-C₁-C₄-alkyl, furyl, furyl-C₁-C₄-alkyl, thienyl,        thiazolyl, piperidinyl, or optionally fluorine-, chlorine-        and/or bromine- or C₁-C₄-alkyl-substituted phenyl,    -   R¹⁷ and R¹⁸ together also represent C₃-C₆-alkanediyl or        C₂-C₅-oxaalkanediyl, each of which is optionally substituted by        C₁-C₄-alkyl, phenyl, furyl, a fused benzene ring or by two        substituents which, together with the C atom to which they are        attached, form a 5- or 6-membered carbocycle,    -   R¹⁹ represents hydrogen, cyano, halogen, or represents in each        case optionally fluorine-, chlorine- and/or bromine-substituted        C₁-C₄-alkyl, C₃-C₆-cycloalkyl or phenyl,    -   R²⁰ represents hydrogen, in each case optionally hydroxy-,        cyano-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₆-alkyl,        C₃-C₆-cycloalkyl or tri(C₁-C₄-alkyl)silyl,    -   R²¹ represents hydrogen, cyano, halogen, or represents in each        case optionally fluorine-, chlorine- and/or bromine-substituted        C₁-C₄-alkyl, C₃-C₆-cycloalkyl or phenyl,    -   X¹ represents nitro, cyano, halogen, C₁-C₄-alkyl,        C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy,    -   X² represents hydrogen, cyano, nitro, halogen, C₁-C₄-alkyl,        C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy,    -   X³ represents hydrogen, cyano, nitro, halogen, C₁-C₄-alkyl,        C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy,    -   and/or the following compounds, defined by general formulae,    -   of the general formula (IId)

-   -   -   or of the general formula (IIe)

-   -   -   where

    -   t represents a number 0, 1, 2, 3, 4 or 5,

    -   v represents a number 0, 1, 2, 3, 4 or 5,

    -   R²² represents hydrogen or C₂-C₄-alkyl,

    -   R²³ represents hydrogen or C₁-C₄-alkyl,

    -   R²⁴ represents hydrogen, in each case optionally cyano-,        halogen- or C₁-C₄-alkoxy-substituted C₁-C₆-alkyl, C₁-C₆-alkoxy,        C₁-C₆-alkylthio, C₁-C₆-alkylamino or di(C₁-C₄-alkyl)amino, or in        each case optionally cyano-, halogen- or C₁-C₄-alkyl-substituted        C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyloxy, C₃-C₆-cycloalkylthio or        C₃-C₆-cycloalkylamino,

    -   R²⁵ represents hydrogen, optionally cyano-, hydroxy-, halogen-        or C₁-C₄-alkoxy-substituted C₁-C₆-alkyl, in each case optionally        cyano- or halogen-substituted C₃-C₆-alkenyl or C₃-C₆-alkynyl, or        optionally cyano-, halogen- or C₁-C₄-alkyl-substituted        C₃-C₆-cycloalkyl,

    -   R²⁶ represents hydrogen, optionally cyano-, hydroxy-, halogen-        or C₁-C₄-alkoxy-substituted C₁-C₆-alkyl, in each case optionally        cyano- or halogen-substituted C₃-C₆-alkenyl or C₃-C₆-alkynyl,        optionally cyano-, halogen- or C₁-C₄-alkyl-substituted        C₃-C₆-cycloalkyl, or optionally nitro-, cyano-, halogen-,        C₁-C₄-alkyl-, C₁-C₄-haloalkyl-, C₁-C₄-alkoxy- or        C₁-C₄-haloalkoxy-substituted phenyl, or together with R²⁵        represents in each case optionally C₁-C₄-alkyl-substituted        C₂-C₆-alkanediyl or C₂-C₅-oxaalkanediyl,

    -   X⁴ represents nitro, cyano, carboxy, carbamoyl, formyl,        sulphamoyl, hydroxy, amino, halogen, C₁-C₄-alkyl,        C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy, and

    -   X⁵ represents nitro, cyano, carboxy, carbamoyl, formyl,        sulphamoyl, hydroxy, amino, halogen, C₁-C₄-alkyl,        C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy.

A general definition of the compounds of the invention is given by theformula (I). Preferred substituents and ranges of the radicals listed inthe formulae mentioned above and below are elucidated in the followingtext:

-   W preferably represents hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl,    C₂-C₆-alkynyl, halogen, C₁-C₆-alkoxy, C₁-C₄-haloalkyl,    C₁-C₄-haloalkoxy or cyano,-   X preferably represents halogen, C₁-C₆-alkyl, C₂-C₆-alkenyl,    C₂-C₆-alkynyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy,    C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl,    C₁-C₆-haloalkoxy, C₃-C₆-haloalkenyloxy, nitro or cyano,-   Y and Z independently of one another preferably represent hydrogen,    halogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy,    C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy, cyano, C₂-C₆-alkenyl,    C₂-C₆-alkynyl or represent one of the (Het)aryl radicals

-   V¹ preferably represents hydrogen, halogen, C₁-C₁₂-alkyl,    C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl,    C₁-C₆-alkylsulphonyl, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, nitro,    cyano or in each case optionally mono- or poly-halogen-,    —C₁-C₆-alkyl-, —C₁-C₆-alkoxy-, —C₁-C₄-haloalkyl-,    —C₁-C₄-haloalkoxy-, -nitro- or -cyano-substituted phenyl, phenoxy,    phenoxy-C₁-C₄-alkyl, phenyl-C₁-C₄-alkoxy, phenylthio-C₁-C₄-alkyl or    phenyl-C₁-C₄-alkylthio,-   V² and V³ independently of one another preferably represent    hydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₄-haloalkyl or    C₁-C₄-haloalkoxy,    -   with the proviso that one of the radicals, Y or Z, represents        one of the (Het)aryl radicals listed,-   A preferably represents a C₁-C₆-alkanediyl radical,-   B preferably represents hydrogen, C₁-C₆-alkyl or    C₁-C₄-alkoxy-C₁-C₄-alkyl,-   D preferably represents in each case optionally mono- to    poly-halogen- or -cyano-substituted C₁-C₆-alkoxy, C₃-C₆-alkenyloxy,    C₃-C₆-alkynyloxy, C₁-C₄-alkoxy-C₂-C₄-alkoxy, represents in each case    optionally mono- to tri-halogen-, —C₁-C₆-alkyl-, —C₁-C₆-alkoxy-,    —C₁-C₄-haloalkyl-, —C₁-C₄-haloalkoxy-, -cyano- or -nitro-substituted    phenoxy, pyridyloxy, pyrimidyloxy, pyrazolyloxy, thiazolyloxy,    thienyloxy, phenyl-C₁-C₄-alkoxy, pyridyl-C₁-C₄-alkoxy,    pyrimidyl-C₁-C₄-alkoxy, pyrazolyl-C₁-C₄-alkoxy, thienyl-C₁-C₄-alkoxy    or represents optionally mono- to tri-halogen-, —C₁-C₄-alkyl-,    —C₁-C₄-alkoxy-, —C₁-C₄-haloalkyl-substituted, saturated or    unsaturated C₃-C₈-cycloalkyl interrupted by one or, optionally, two    oxygen atoms, or-   A preferably represents a bond,-   B preferably represents hydrogen or C₁-C₄-alkyl,-   D preferably represents optionally mono- to tri-C₁-C₂-alkyl- or    —C₁-C₂-alkoxy-substituted, saturated or unsaturated C₃-C₈-cycloalkyl    interrupted by one or, optionally, two oxygen atoms,-   G preferably represents hydrogen (a) or represents one of the groups

-   -   in which    -   E represents a metal ion or an ammonium ion,    -   L represents oxygen or sulphur and    -   M represents oxygen or sulphur,

-   R¹ preferably represents in each case optionally halogen- or    cyano-substituted C₁-C₂₀-alkyl, C₂-C₂₀-alkenyl,    C₁-C₈-alkoxy-C₁-C₈-alkyl, C₁-C₈-alkylthio-C₁-C₈-alkyl or    poly-C₁-C₈-alkoxy-C₁-C₈-alkyl or represents optionally halogen-,    C₁-C₆-alkyl- or C₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl, in which    optionally one or two methylene groups not directly adjacent are    replaced by oxygen and/or sulphur,    -   represents optionally halogen-, cyano-, nitro-, C₁-C₆-alkyl-,        C₁-C₆-alkoxy-, C₁-C₆-haloalkyl-, C₁-C₆-haloalkoxy-,        C₁-C₆-alkylthio- or C₁-C₆-alkylsulphonyl-substituted phenyl,    -   represents optionally halogen-, nitro-, cyano-, C₁-C₆-alkyl-,        C₁-C₆-alkoxy-, C₁-C₆-haloalkyl- or C₁-C₆-haloalkoxy-substituted        phenyl-C₁-C₆-alkyl,    -   represents optionally halogen- or C₁-C₆-alkyl-substituted 5- or        6-membered hetaryl having one or two heteroatoms from the series        of oxygen, sulphur and nitrogen,    -   represents optionally halogen- or C₁-C₆-alkyl-substituted        phenoxy-C₁-C₆-alkyl or    -   represents optionally halogen-, amino- or        C₁-C₆-alkyl-substituted 5- or 6-membered hetaryloxy-C₁-C₆-alkyl        having one or two heteroatoms from the series of oxygen, sulphur        and nitrogen,

-   R² preferably represents in each case optionally halogen- or    cyano-substituted C₁-C₂₀-alkyl, C₂-C₂₀-alkenyl,    C₁-C₈-alkoxy-C₂-C₈-alkyl or poly-C₁-C₈-alkoxy-C₂-C₈-alkyl,    -   represents optionally halogen-, C₁-C₆-alkyl- or        C₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl or    -   represents in each case optionally halogen-, cyano-, nitro-,        C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₆-haloalkyl- or        C₁-C₆-haloalkoxy-substituted phenyl or benzyl,

-   R³ preferably represents optionally halogen-substituted C₁-C₈-alkyl    or in each case optionally halogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-,    C₁-C₄-haloalkyl-, C₁-C₄-haloalkoxy-, cyano- or nitro-substituted    phenyl or benzyl,

-   R⁴ and R⁵ independently of one another preferably represent in each    case optionally halogen-substituted C₁-C₈-alkyl, C₁-C₈-alkoxy,    C₁-C₈-alkylamino, di(C₁-C₈-alkyl)amino, C₁-C₈-alkylthio or    C₃-C₈-alkenylthio or represent in each case optionally halogen-,    nitro-, cyano-, C₁-C₄-alkoxy-, C₁-C₄-haloalkoxy-, C₁-C₄-alkylthio-,    C₁-C₄-haloalkylthio-, C₁-C₄-alkyl- or C₁-C₄-haloalkyl-substituted    phenyl, phenoxy or phenylthio,

-   R⁶ and R⁷ independently of one another preferably represent    hydrogen, represent in each case optionally halogen- or    cyano-substituted C₁-C₈-alkyl, C₃-C₈-cycloalkyl, C₁-C₈-alkoxy,    C₃-C₈-alkenyl or C₁-C₈-alkoxy-C₂-C₈-alkyl, represent in each case    optionally halogen-, C₁-C₈-alkyl-, C₁-C₈-haloalkyl- or    C₁-C₈-alkoxy-substituted phenyl or benzyl or together represent an    optionally C₁-C₆-alkyl-substituted C₃-C₆-alkylene radical in which    optionally a methylene group is replaced by oxygen or sulphur.

In the radical definitions stated as being preferable, halogen or halorepresents fluorine, chlorine, bromine and iodine, in particularfluorine, chlorine and bromine.

-   W particularly preferably represents hydrogen, chlorine, bromine,    C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₁-C₄-alkoxy,    C₁-C₂-haloalkyl or C₁-C₂-haloalkoxy,-   X particularly preferably represents chlorine, bromine, C₁-C₄-alkyl,    C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl,    C₁-C₄-haloalkoxy or cyano,-   Y and Z independently of one another particularly preferably    represent hydrogen, fluorine, chlorine, bromine, C₁-C₄-alkyl,    C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₁-C₆-alkoxy, C₁-C₄-haloalkyl,    C₁-C₄-haloalkoxy, cyano, C₂-C₄-alkenyl, C₂-C₄-alkynyl or represent    one of the (Het)aryl radicals

-   V¹ particularly preferably represents hydrogen, fluorine, chlorine,    bromine, C₁-C₆-alkyl, C₁-C₄-alkoxy, C₁-C₂-haloalkyl,    C₁-C₂-haloalkoxy, nitro, cyano or in each case optionally mono- to    di-fluorine-, -chlorine-, -bromine-, —C₁-C₄-alkyl-, —C₁-C₄-alkoxy-,    —C₁-C₂-haloalkyl-, —C₁-C₂-haloalkoxy-, -nitro- or -cyano-substituted    phenyl,-   V² and V³ independently of one another particularly preferably    represent hydrogen, fluorine, chlorine, bromine, C₁-C₄-alkyl,    C₁-C₄-alkoxy, C₁-C₂-haloalkyl or C₁-C₂-haloalkoxy,    -   with the proviso that one of the radicals, Y or Z, represents        one of the (Het)aryl radicals listed,-   A particularly preferably represents a C₁-C₄-alkanediyl radical,-   B particularly preferably represents hydrogen, C₁-C₄-alkyl or    C₁-C₄-alkoxy-C₁-C₂-alkyl,-   D particularly preferably represents in each case optionally mono-    to penta-fluorine-, -chlorine- or -cyano-substituted C₁-C₄-alkoxy,    C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, C₁-C₃-alkoxy-C₂-C₃-alkoxy,    represents optionally mono- to di-fluorine-, -chlorine-, -bromine-,    —C₁-C₄-alkyl-, —C₁-C₄-alkoxy-, -trifluoromethyl- or    -trifluoromethoxy-substituted phenoxy or represents optionally mono-    to di-fluorine-, -chlorine-, -methyl-, -ethyl-, -methoxy- or    -trifluoromethyl-substituted, saturated C₄-C₇-cycloalkyl interrupted    by one or, optionally, two oxygen atoms, or-   A particularly preferably represents a bond,-   B particularly preferably represents hydrogen or C₁-C₂-alkyl,-   D particularly preferably represents optionally mono- to di-methyl-    or -ethyl-substituted, saturated C₅-C₆-cycloalkyl interrupted by one    or, optionally, two oxygen atoms,-   G particularly preferably represents hydrogen (a) or represents one    of the groups

-   -   in which    -   E represents a metal ion or an ammonium ion,    -   L represents oxygen or sulphur and    -   M represents oxygen or sulphur,

-   R¹ particularly preferably represents in each case optionally mono-    to tri-fluorine- or -chlorine-substituted C₁-C₁₆-alkyl,    C₂-C₁₆-alkenyl, C₁-C₆-alkoxy-C₁-C₄-alkyl,    C₁-C₆-alkylthio-C₁-C₄-alkyl or poly-C₁-C₆-alkoxy-C₁-C₄-alkyl or    represents optionally mono- to di-fluorine-, -chlorine-,    —C₁-C₅-alkyl- or —C₁-C₅-alkoxy-substituted C₃-C₇-cycloalkyl in which    optionally one or two methylene groups not directly adjacent are    replaced by oxygen and/or sulphur,    -   represents optionally mono- to tri-fluorine-, -chlorine-,        -bromine-, -cyano-, -nitro-, —C₁-C₄-alkyl-, —C₁-C₄-alkoxy-,        —C₁-C₃-haloalkyl-, —C₁-C₃-haloalkoxy-, —C₁-C₄-alkylthio- or        —C₁-C₄-alkylsulphonyl-substituted phenyl,    -   represents optionally mono- to di-fluorine-, -chlorine-,        -bromine-, —C₁-C₄-alkyl-, —C₁-C₄-alkoxy-, —C₁-C₃-haloalkyl- or        —C₁-C₃-haloalkoxy-substituted phenyl-C₁-C₄-alkyl,    -   represents in each case optionally mono- to di-fluorine-,        -chlorine-, -bromine- or —C₁-C₄-alkyl-substituted pyrazolyl,        thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl,    -   represents optionally mono- to di-fluorine-, -chlorine-,        -bromine- or —C₁-C₄-alkyl-substituted phenoxy-C₁-C₅-alkyl or    -   represents in each case optionally mono- to di-fluorine-,        -chlorine-, -bromine-, -amino- or —C₁-C₄-alkyl-substituted        pyridyloxy-C₁-C₅-alkyl, pyrimidyloxy-C₁-C₅-alkyl or        thiazolyloxy-C₁-C₅-alkyl,

-   R² particularly preferably represents in each case optionally mono-    to tri-fluorine- or -chlorine-substituted C₁-C₁₆-alkyl,    C₂-C₁₆-alkenyl, C₁-C₆-alkoxy-C₂-C₆-alkyl or    poly-C₁-C₆-alkoxy-C₂-C₆-alkyl,    -   represents optionally mono- to di-fluorine-, -chlorine-,        —C₁-C₄-alkyl- or —C₁-C₄-alkoxy-substituted C₃-C₇-cycloalkyl or    -   represents in each case optionally mono- to tri-fluorine-,        -chlorine-, -bromine-, -cyano-, -nitro-, —C₁-C₄-alkyl-,        —C₁-C₃-alkoxy-, —C₁-C₃-haloalkyl- or        —C₁-C₃-haloalkoxy-substituted phenyl or benzyl,

-   R³ particularly preferably represents optionally mono- to    tri-fluorine- or -chlorine-substituted C₁-C₆-alkyl or in each case    optionally mono- to di-fluorine-, -chlorine-, -bromine-,    —C₁-C₄-alkyl-, —C₁-C₄-alkoxy-, —C₁-C₂-haloalkoxy-,    —C₁-C₂-haloalkyl-, -cyano- or -nitro-substituted phenyl or benzyl,

-   R⁴ and R⁵ independently of one another particularly preferably    represent in each case optionally mono- to tri-fluorine- or    -chlorine-substituted C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylamino,    di(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio or C₃-C₄-alkenylthio or    represent in each case optionally mono- to di-fluorine-, -chlorine-,    -bromine-, -nitro-, -cyano-, —C₁-C₃-alkoxy-, —C₁-C₃-haloalkoxy-,    —C₁-C₃-alkylthio-, —C₁-C₃-haloalkylthio-, —C₁-C₃-alkyl- or    —C₁-C₃-haloalkyl-substituted phenyl, phenoxy or phenylthio,

-   R⁶ and R⁷ independently of one another particularly preferably    represent hydrogen, represent in each case optionally mono- to    tri-fluorine- or -chlorine-substituted C₁-C₆-alkyl,    C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₃-C₆-alkenyl or    C₁-C₆-alkoxy-C₂-C₆-alkyl, represent in each case optionally mono- to    tri-fluorine-, -chlorine-, -bromine-, —C₁-C₅-haloalkyl-,    —C₁-C₅-alkyl- or —C₁-C₅-alkoxy-substituted phenyl or benzyl, or    together represent an optionally C₁-C₄-alkyl-substituted    C₃-C₆-alkylene radical in which optionally a methylene group is    replaced by oxygen or sulphur.

In the radical definitions stated as being particularly preferable,halogen or halo represents fluorine, chlorine and bromine, in particularfluorine and chlorine.

-   W very preferably represents hydrogen, chlorine, bromine, methyl,    ethyl, methoxy, ethoxy or trifluoromethyl,-   X very preferably represents chlorine, bromine, methyl, ethyl,    propyl, methoxy, ethoxy, trifluoromethyl, difluoromethoxy,    trifluoromethoxy or cyano,-   Y and Z independently of one another very preferably represent    hydrogen, fluorine, chlorine, bromine, methyl, ethyl, methoxy,    trifluoromethyl, trifluoromethoxy, cyano or a phenyl radical,

-   V¹ very preferably represents hydrogen, fluorine, chlorine, bromine,    methyl, ethyl, n-propyl, isopropyl, tert-butyl, methoxy, ethoxy,    n-propoxy, isopropoxy, trifluoromethyl or trifluoromethoxy,-   V² very preferably represents hydrogen, fluorine, chlorine, methyl,    ethyl, n-propyl, isopropyl, methoxy, ethoxy or trifluoromethyl,    -   with the proviso that one of the radicals, Y or Z, represents an        optionally substituted phenyl radical,-   A very preferably represents    -   —CH₂—, —CH₂—CH₂—, —CH₂—CH₂—CH₂—, —CH₂—CHCH₃—, —CHCH₃—CH₂—,        —CH₂—C(CH₃)₂—, —C(CH₃)₂—CH₂—,-   B very preferably represents hydrogen, methyl or ethyl,-   D very preferably represents methoxy, ethoxy, propoxy, isopropoxy,    butoxy, isobutoxy, allyloxy, methallyloxy, isoprenyloxy,    propargyloxy, butenyloxy, methoxyethoxy, ethoxyethoxy, represents    phenoxy optionally monosubstituted by fluorine, chlorine, bromine,    methyl, methoxy, trifluoromethyl or trifluoromethoxy, or represents    in each case optionally mono- to di-methyl-substituted    tetrahydrofuranyl, tetrahydropyranyl, dioxolanyl or dioxanyl, or-   A very preferably represents a bond,-   B very preferably represents hydrogen, methyl or ethyl,-   D very preferably represents tetrahydrofuranyl, tetrahydropyranyl,    dioxolanyl or dioxanyl,-   G very preferably represents hydrogen (a) or represents one of the    groups

-   -   in which    -   E represents a metal ion or an ammonium ion,    -   L represents oxygen or sulphur and    -   M represents oxygen or sulphur,

-   R¹ very preferably represents in each case optionally mono- to    tri-fluorine- or -chlorine-substituted C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl,    C₁-C₄-alkoxy-C₁-C₂-alkyl, C₁-C₄-alkylthio-C₁-C₂-alkyl or represents    C₃-C₆-cycloalkyl optionally monosubstituted by fluorine, chlorine,    methyl, ethyl or methoxy,    -   represents optionally mono- to di-fluorine-, -chlorine-,        -bromine-, -cyano-, -nitro-, -methyl-, -ethyl-, -n-propyl-,        -isopropyl-, -methoxy-, -ethoxy-, -trifluoromethyl- or        -trifluoromethoxy-substituted phenyl,    -   represents furanyl, thienyl or pyridyl in each case optionally        monosubstituted by chlorine, bromine or methyl,

-   R² very preferably represents in each case optionally mono- to    tri-fluorine- or -chlorine-substituted C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl    or C₁-C₄-alkoxy-C₂-C₄-alkyl,    -   represents cyclopentyl or cyclohexyl    -   or represents in each case optionally mono- to di-fluorine-,        -chlorine-, -cyano-, -nitro-, -methyl-, -ethyl-, -methoxy-,        -trifluoromethyl- or -trifluoromethoxy-substituted phenyl or        benzyl,

-   R³ very preferably represents in each case optionally mono- to    tri-fluorine- or -chlorine-substituted methyl, ethyl, propyl or    isopropyl, or phenyl in each case optionally monosubstituted by    fluorine, chlorine, bromine, methyl, ethyl, isopropyl, tert-butyl,    methoxy, ethoxy, isopropoxy, trifluoromethyl, trifluoromethoxy,    cyano or nitro,

-   R⁴ and R⁵ independently of one another very preferably represent    C₁-C₄-alkoxy or C₁-C₄-alkyl-thio or represent phenyl, phenoxy or    phenylthio in each case optionally monosubstituted by fluorine,    chlorine, bromine, nitro, cyano, methyl, methoxy, trifluoromethyl or    trifluoromethoxy,

-   R⁶ and R⁷ independently of one another very preferably represent    hydrogen, represent C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-alkoxy,    C₃-C₄-alkenyl or C₁-C₄-alkoxy-C₂-C₄-alkyl, represent in each case    optionally mono- to di-fluorine-, -chlorine-, -bromine-, -methyl-,    -methoxy- or -trifluoromethyl-substituted phenyl, or together    represent a C₅-C₆-alkylene radical in which optionally a methylene    group is replaced by oxygen or sulphur.

-   W notably represents hydrogen, methyl or ethyl,

-   X notably represents chlorine, methyl or ethyl,

-   Y and Z independently of one another notably represent hydrogen or    one of the following phenyl radicals

-   -   with the proviso that one of the radicals, Y or Z, represents an        optionally substituted phenyl radical,

-   A notably represents    -   —CH₂— or —CH₂—CH₂—,

-   B notably represents methyl,

-   D notably represents methoxy or tetrahydrofuranyl, or

-   A notably represents a bond,

-   B notably represents methyl or ethyl,

-   D notably represents tetrahydrofuranyl,

-   G notably represents hydrogen (a) or represents one of the groups

in which

-   R¹ notably represents C₁-C₁₀-alkyl, C₁-C₄-alkoxy-C₁-C₂-alkyl,    cyclopropyl or    -   represents phenyl optionally monosubstituted by chlorine,-   R² notably represents C₁-C₁₀-alkyl or benzyl.

The general radical definitions and/or elucidations set out above, orthose set out in ranges of preference, can be combined with one anotherarbitrarily, i.e. including combinations between the respective rangesand ranges of preference. They apply to the end products and also to theprecursors and intermediates correspondingly.

Preference in accordance with the invention is given to the compounds ofthe formula (I) in which there is a combination of the definitions setout above as being preferred (preferable).

Particular preference in accordance with the invention is given to thecompounds of the formula (I) in which there is a combination of thedefinitions set out above as being particularly preferred.

Very particular preference is given in accordance with the invention tothe compounds of the formula (I) in which there is a combination of thedefinitions set out above as being very preferred.

Noteworthiness in accordance with the invention is accorded to thecompounds of the formula (I) in which there is a combination of thedefinitions set out above as being notable.

Compounds of the formula (I) in which G represents hydrogen are notable.

Saturated or unsaturated hydrocarbon radicals such as alkyl, alkanediylor alkenyl, both alone and in conjunction with heteroatoms, such as inalkoxy, for example, can as far as possible be straight-chain orbranched in each case.

Optionally substituted radicals can be substituted one or more timesunless indicated otherwise, and in the case of multiple substitutionsthe substituents can be identical or different.

Specifically, as well as the compounds specified in the PreparationExamples, mention may be made of the following compounds of the formula(I-1-a):

TABLE 1 (I-a)

A B D X W Y Z —CH₂— CH₃ OCH₃ CH₃ CH₃ 4-Cl—C₆H₄ H —CH₂— CH₃ OCH₃ C₂H₅ CH₃4-Cl—C₆H₄ H —CH₂— CH₃ OCH₃ C₂H₅ C₂H₅ 4-Cl—C₆H₄ H —CH₂— CH₃ OCH₃ Cl CH₃4-Cl—C₆H₄ H —CH₂— CH₃ OCH₃ Cl C₂H₅ 4-Cl—C₆H₄ H —CH₂— CH₃ OCH₃ CH₃ H H4-Cl—C₆H₄ —CH₂— CH₃ OCH₃ CH₃ CH₃ H 4-Cl—C₆H₄ —CH₂— CH₃ OCH₃ CH₃ H CH₃4-Cl—C₆H₄ —CH₂— CH₃ OCH₃ CH₃ CH₃ CH₃ 4-Cl—C₆H₄ —CH₂— CH₃ OCH₃ Cl H H4-Cl—C₆H₄ —CH₂— CH₃ OCH₃ CH₃ H H 4-F—C₆H₄ —CH₂— CH₃ OCH₃ CH₃ H H4-CH₃—C₆H₄ —CH₂— CH₃ OCH₃ CH₃ H H 4-OCH₃—C₆H₄ —CH₂— CH₃ OCH₃ CH₃ H H4-OCF₃—C₆H₄ —CH₂— CH₃ OCH₃ CH₃ H H 4-CF₃—C₆H₄ —CH₂— CH₃ OCH₃ CH₃ H H3-Cl—C₆H₄ —CH₂— CH₃ OCH₃ CH₃ H H 3-F—C₆H₄ —CH₂— CH₃ OCH₃ CH₃ H H3-OCH₃—C₆H₄ —CH₂— CH₃ OCH₃ CH₃ H H 3-CF₃—C₆H₄ —CH₂— CH₃ OCH₃ CH₃ H H3,4-F₂—C₆H₃ —CH₂— CH₃ OCH₃ CH₃ H H 3,4-Cl₂—C₆H₃ —CH₂— CH₃ OCH₃ CH₃ H H3-F,4-Cl—C₆H₃ —CH₂— CH₃ OCH₃ CH₃ H H 4-Cl,3-F—C₆H₃ —CH₂— CH₃ OCH₃ CH₃ HH 4-CF₃-3-F—C₆H₃ —CH₂— CH₃ OCH₃ CH₃ H H 2,4-F₂—C₆H₃ —CH₂— CH₃ OCH₃ CH₃ HH 3,5-F₂—C₆H₃ —CH₂— CH₃ OCH₃ CH₃ H H 2,5-F₂—C₆H₃ —CH₂— CH₃ OCH₃ CH₃ H H3,4,5-F₃—C₆H₂ —CH₂— CH₃ OCH₃ CH₃ CH₃ H 4-F—C₆H₄ —CH₂— CH₃ OCH₃ CH₃ CH₃ H4-CH₃—C₆H₄ —CH₂— CH₃ OCH₃ CH₃ CH₃ H 4-OCH₃—C₆H₄ —CH₂— CH₃ OCH₃ CH₃ H H4-OCF₃—C₆H₄ —CH₂— CH₃ OCH₃ CH₃ CH₃ H 4-CF₃—C₆H₄ —CH₂— CH₃ OCH₃ CH₃ CH₃ H3-Cl—C₆H₄ —CH₂— CH₃ OCH₃ CH₃ CH₃ H 3-F—C₆H₄ —CH₂— CH₃ OCH₃ CH₃ CH₃ H3-OCH₃—C₆H₄ —CH₂— CH₃ OCH₃ CH₃ CH₃ H 3-CF₃—C₆H₂ —CH₂— CH₃ OCH₃ CH₃ CH₃ H3,4-F₂—C₆H₃ —CH₂— CH₃ OCH₃ CH₃ CH₃ H 3,4-Cl₂—C₆H₃ —CH₂— CH₃ OCH₃ CH₃ CH₃H 3-F,4-Cl—C₆H₃ —CH₂— CH₃ OCH₃ CH₃ CH₃ H 4-Cl,3-F—C₆H₃ —CH₂— CH₃ OCH₃CH₃ CH₃ H 4-CF₃-3-F—C₆H₃ —CH₂— CH₃ OCH₃ CH₃ CH₃ H 2,4-F₂—C₆H₃ —CH₂— CH₃OCH₃ CH₃ CH₃ H 3,5-F₂—C₆H₃ —CH₂— CH₃ OCH₃ CH₃ CH₃ H 2,5-F₂—C₆H₃ —CH₂—CH₃ OCH₃ CH₃ CH₃ H 3,4,5-F₃—C₆H₂ —CH₂— CH₃ OCH₃ Cl H H 4-F—C₆H₄ —CH₂—CH₃ OCH₃ Cl H H 4-CH₃—C₆H₄ —CH₂— CH₃ OCH₃ Cl H H 4-OCH₃—C₆H₄ —CH₂— CH₃OCH₃ Cl H H 4-OCF₃—C₆H₄ —CH₂— CH₃ OCH₃ Cl H H 4-CF₃—C₆H₂ —CH₂— CH₃ OCH₃Cl H H 3-Cl—C₆H₄ —CH₂— CH₃ OCH₃ Cl H H 3-F—C₆H₄ —CH₂— CH₃ OCH₃ Cl H H3-OCH₃—C₆H₄ —CH₂— CH₃ OCH₃ Cl H H 3-CF₃—C₆H₄ —CH₂— CH₃ OCH₃ Cl H H3,4-F₂—C₆H₃ —CH₂— CH₃ OCH₃ Cl H H 3,4-Cl₂—C₆H₃ —CH₂— CH₃ OCH₃ Cl H H3-F,4-Cl—C₆H₃ —CH₂— CH₃ OCH₃ Cl H H 4-Cl,3-F—C₆H₃ —CH₂— CH₃ OCH₃ Cl H H4-CF₃-3-F—C₆H₃ —CH₂— CH₃ OCH₃ Cl H H 2,4-F₂—C₆H₃ —CH₂— CH₃ OCH₃ Cl H H3,5-F₂—C₆H₃ —CH₂— CH₃ OCH₃ Cl H H 2,5-F₂—C₆H₃ —CH₂— CH₃ OCH₃ Cl H H3,4,5-F₃—C₆H₂ —CH₂— CH₃ OCH₃ CH₃ H 4-F—C₆H₄ H —CH₂— CH₃ OCH₃ CH₃ H4-CH₃—C₆H₄ H —CH₂— CH₃ OCH₃ CH₃ H 4-OCH₃—C₆H₄ H —CH₂— CH₃ OCH₃ CH₃ H4-OCF₃—C₆H₄ H —CH₂— CH₃ OCH₃ CH₃ H 4-CF₃—C₆H₄ H —CH₂— CH₃ OCH₃ CH₃ H3-Cl—C₆H₄ H —CH₂— CH₃ OCH₃ CH₃ H 3-F—C₆H₄ H —CH₂— CH₃ OCH₃ CH₃ H3-OCH₃—C₆H₄ H —CH₂— CH₃ OCH₃ CH₃ H 3-CF₃—C₆H₄ H —CH₂— CH₃ OCH₃ CH₃ H3,4-F₂—C₆H₃ H —CH₂— CH₃ OCH₃ CH₃ H 3,4-Cl₂—C₆H₃ H —CH₂— CH₃ OCH₃ CH₃ H3-F,4-Cl—C₆H₃ H —CH₂— CH₃ OCH₃ CH₃ H 4-Cl,3-F—C₆H₃ H —CH₂— CH₃ OCH₃ CH₃H 4-CF₃-3-F—C₆H₃ H —CH₂— CH₃ OCH₃ CH₃ H 2,4-F₂—C₆H₃ H —CH₂— CH₃ OCH₃ CH₃H 3,5-F₂—C₆H₃ H —CH₂— CH₃ OCH₃ CH₃ H 2,5-F₂—C₆H₃ H —CH₂— CH₃ OCH₃ CH₃ H3,4,5-F₃—C₆H₂ H —CH₂— CH₃ OCH₃ CH₃ CH₃ 4-F—C₆H₄ H —CH₂— CH₃ OCH₃ CH₃ CH₃4-CH₃—C₆H₄ H —CH₂— CH₃ OCH₃ CH₃ CH₃ 4-OCH₃—C₆H₄ H —CH₂— CH₃ OCH₃ CH₃ CH₃4-OCF₃—C₆H₄ H —CH₂— CH₃ OCH₃ CH₃ CH₃ 4-CF₃—C₆H₄ H —CH₂— CH₃ OCH₃ CH₃ CH₃3-Cl—C₆H₄ H —CH₂— CH₃ OCH₃ CH₃ CH₃ 3-F—C₆H₄ H —CH₂— CH₃ OCH₃ CH₃ CH₃3-OCH₃—C₆H₄ H —CH₂— CH₃ OCH₃ CH₃ CH₃ 3-CF₃—C₆H₄ H —CH₂— CH₃ OCH₃ CH₃ CH₃3,4-F₂—C₆H₃ H —CH₂— CH₃ OCH₃ CH₃ CH₃ 3,4-Cl₂—C₆H₃ H —CH₂— CH₃ OCH₃ CH₃CH₃ 3-F,4-Cl—C₆H₃ H —CH₂— CH₃ OCH₃ CH₃ CH₃ 4-Cl,3-F—C₆H₃ H —CH₂— CH₃OCH₃ CH₃ CH₃ 4-CF₃-3-F—C₆H₃ H —CH₂— CH₃ OCH₃ CH₃ CH₃ 2,4-F₂—C₆H₃ H —CH₂—CH₃ OCH₃ CH₃ CH₃ 3,5-F₂—C₆H₃ H —CH₂— CH₃ OCH₃ CH₃ CH₃ 2,5-F₂—C₆H₃ H—CH₂— CH₃ OCH₃ CH₃ CH₃ 3,4,5-F₃—C₆H₂ H —CH₂— CH₃ OCH₃ Cl H 4-F—C₆H₄ H—CH₂— CH₃ OCH₃ Cl H 4-CH₃—C₆H₄ H —CH₂— CH₃ OCH₃ Cl H 4-OCH₃—C₆H₄ H —CH₂—CH₃ OCH₃ Cl H 4-OCF₃—C₆H₄ H —CH₂— CH₃ OCH₃ Cl H 4-CF₃—C₆H₄ H —CH₂— CH₃OCH₃ Cl H 3-Cl—C₆H₄ H —CH₂— CH₃ OCH₃ Cl H 3-F—C₆H₄ H —CH₂— CH₃ OCH₃ Cl H3-OCH₃—C₆H₄ H —CH₂— CH₃ OCH₃ Cl H 3-CF₃—C₆H₄ H —CH₂— CH₃ OCH₃ Cl H3,4-F₂—C₆H₃ H —CH₂— CH₃ OCH₃ Cl H 3,4-Cl₂—C₆H₃ H —CH₂— CH₃ OCH₃ Cl H3-F,4-Cl—C₆H₃ H —CH₂— CH₃ OCH₃ Cl H 4-Cl,3-F—C₆H₃ H —CH₂— CH₃ OCH₃ Cl H4-CF₃-3-F—C₆H₃ H —CH₂— CH₃ OCH₃ Cl H 2,4-F₂—C₆H₃ H —CH₂— CH₃ OCH₃ Cl H3,5-F₂—C₆H₃ H —CH₂— CH₃ OCH₃ Cl H 2,5-F₂—C₆H₃ H —CH₂— CH₃ OCH₃ Cl H3,4,5-F₃—C₆H₂ H

TABLE 2 W, X, Y and Z as indicated in Table 1 A = —CH₂—; B = CH₃, D =OC₂H₅

TABLE 3 W, X, Y and Z as indicated in Table 1 A = —CH₂—CH₂—; B = CH₃, D= O₂CH₅

TABLE 4 W, X, Y and Z as indicated in Table 1 A = —CH₂—CH₂—; B = CH₃, D= OC₂H₅

TABLE 5

TABLE 6

TABLE 7

TABLE 8

Preferred definitions of the groups listed above in connection with thecrop plant tolerance promoter compounds (herbicide safeners) of theformulae (IIa), (IIb), (IIc), (IId) and (IIe) are defined below.

-   m preferably represents the numbers 0, 1, 2, 3 or 4.-   A¹ preferably represents one of the divalent heterocyclic groupings    shown below

-   n preferably represents the numbers 0, 1, 2, 3 or 4.-   A² preferably represents in each case optionally methyl-, ethyl-,    methoxycarbonyl- or ethoxycarbonyl- or allyloxycarbonyl-substituted    methylene or ethylene.-   R¹⁴ preferably represents hydroxyl, mercapto, amino, methoxy,    ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio,    ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio,    methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or    t-butylamino, dimethylamino or diethylamino.-   R¹⁵ preferably represents hydroxyl, mercapto, amino, methoxy,    ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, 1-methylhexyloxy,    allyloxy, 1-allyloxymethylethoxy, methylthio, ethylthio, n- or    i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n-    or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or    diethylamino.-   R¹⁶ preferably represents in each case optionally fluorine-,    chlorine- and/or bromine-substituted methyl, ethyl, n- or i-propyl.-   R¹⁷ preferably represents hydrogen, in each case optionally    fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl,    n-, i-, s- or t-butyl, propenyl, butenyl, propynyl or butynyl,    methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl,    dioxolanylmethyl, furyl, furyl-methyl, thienyl, thiazolyl,    piperidinyl, or optionally fluorine-, chlorine-, methyl-, ethyl-, n-    or i-propyl-, n-, i-, s- or t-butyl-substituted phenyl.-   R¹⁸ preferably represents hydrogen, in each case optionally    fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl,    n-, i-, s- or t-butyl, propenyl, butenyl, propynyl or butynyl,    methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl,    dioxolanylmethyl, furyl, furyl-methyl, thienyl, thiazolyl,    piperidinyl, or optionally fluorine-, chlorine-, methyl-, ethyl-, n-    or i-propyl-, n-, i-, s- or t-butyl-substituted phenyl, or together    with R¹⁷ represents one of the radicals —CH₂—O—CH₂—CH₂— and    —CH₂—CH₂—O—CH₂—CH₂— which are optionally substituted by methyl,    ethyl, furyl, phenyl, a fused benzene ring or by two substituents    which, together with the C atom to which they are attached, form a    5- or 6-membered carbocycle.-   R¹⁹ preferably represents hydrogen, cyano, fluorine, chlorine,    bromine, or represents in each case optionally fluorine-, chlorine-    and/or bromine-substituted methyl, ethyl, n- or i-propyl,    cyclo-propyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl.-   R²⁰ preferably represents hydrogen, optionally hydroxyl-, cyano-,    fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted    methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.-   R²¹ preferably represents hydrogen, cyano, fluorine, chlorine,    bromine, or represents in each case optionally fluorine-, chlorine-    and/or bromine-substituted methyl, ethyl, n- or i-propyl, n-, i-, s-    or t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or    phenyl.-   X¹ preferably represents nitro, cyano, fluorine, chlorine, bromine,    methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,    difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl,    chloro-difluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or    i-propoxy, difluoromethoxy or trifluoromethoxy.-   X² preferably represents hydrogen, nitro, cyano, fluorine, chlorine,    bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,    difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl,    chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or    i-propoxy, difluoro-methoxy or trifluoromethoxy.-   X³ preferably represents hydrogen, nitro, cyano, fluorine, chlorine,    bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,    difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl,    chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or    i-propoxy, difluoromethoxy or trifluoromethoxy.-   t preferably represents the numbers 0, 1, 2, 3 or 4.-   v preferably represents the numbers 0, 1, 2 or 3.-   R²² preferably represents hydrogen, methyl, ethyl, n- or i-propyl.-   R²³ preferably represents hydrogen, methyl, ethyl, n- or i-propyl.-   R²⁴ preferably represents hydrogen, in each case optionally cyano-,    fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted    methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy,    ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio,    ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio,    methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or    t-butylamino, dimethylamino or diethylamino, or in each case    optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-,    n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl,    cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy,    cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio,    cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino    or cyclohexylamino.-   R²⁵ preferably represents hydrogen, in each case optionally cyano-,    hydroxyl-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or    i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or    s-butyl, in each case optionally cyano-, fluorine-, chlorine- or    bromine-substituted propenyl, butenyl, propynyl or butynyl, or in    each case optionally cyano-, fluorine-, chlorine-, bromine-,    methyl-, ethyl-, n- or i-propyl-substituted cyclopropyl, cyclobutyl,    cyclopentyl or cyclohexyl.-   R²⁶ preferably represents hydrogen, in each case optionally cyano-,    hydroxyl-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or    i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or    s-butyl, in each case optionally cyano-, fluorine-, chlorine- or    bromine-substituted propenyl, butenyl, propynyl or butynyl, in each    case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-,    ethyl-, n- or i-propyl-substituted cyclopropyl, cyclobutyl,    cyclopentyl or cyclohexyl, or optionally nitro-, cyano-, fluorine-,    chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or    t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-,    difluoromethoxy- or trifluoromethoxy-substituted phenyl, or together    with R²⁵ represents in each case optionally methyl- or    ethyl-substituted butane-1,4-diyl (trimethylene), pentane-1,5-diyl,    1-oxabutane-1,4-diyl or 3-oxapentane-1,5-diyl.-   X⁴ preferably represents nitro, cyano, carboxy, carbamoyl, formyl,    sulphamoyl, hydroxyl, amino, fluorine, chlorine, bromine, methyl,    ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl,    methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or    trifluoromethoxy.-   X⁵ preferably represents nitro, cyano, carboxyl, carbamoyl, formyl,    sulphamoyl, hydroxyl, amino, fluorine, chlorine, bromine, methyl,    ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl,    methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or    trifluoromethoxy.

Examples of the compounds of the formula (IIa) which are veryparticularly preferred as herbicide safeners according to the inventionare listed in the table below.

TABLE Examples of the compounds of the formula (IIa) Example (positions)No. (X¹)_(m) A¹ R¹⁴ IIa-1 (2) Cl, (4) Cl

OCH₃ IIa-2 (2) Cl, (4) Cl

OCH₃ IIa-3 (2) Cl, (4) Cl

OC₂H₅ IIa-4 (2) Cl, (4) Cl

OC₂H₅ IIa-5 (2) Cl

OCH₃ IIa-6 (2) Cl, (4) Cl

OCH₃ IIa-7 (2) F

OCH₃ IIa-8 (2)F

OCH₃ IIa-9 (2) Cl, (4) Cl

OC₂H₅ IIa-10 (2) Cl, (4) CF₃

OCH₃ IIa-11 (2)Cl

OCH₃ IIa-12 —

OC₂H₅ IIa-13 (2) Cl, (4) Cl

OC₂H₅ IIa-14 (2) Cl, (4) Cl

OC₂H₅ IIa-15 (2) Cl, (4) Cl

OC₂H₅ IIa-16 (2) Cl, (4) Cl

OC₂H₅ IIa-17 (2) Cl, (4) Cl

OC₂H₅ IIa-18 —

OH

Examples of the compounds of the formula (IIb) which are veryparticularly preferred as herbicide safeners according to the inventionare listed in the table below.

TABLE Examples of the compounds of the formula (IIb) (Po- si- Exampletion) (Position) No. X² X³ A² R¹⁵ IIb-1 (5) — CH₂ OH Cl IIb-2 (5) — CH₂OCH₃ Cl IIb-3 (5) — CH₂ OC₂H₅ Cl IIb-4 (5) — CH₂ OC₃H₇-n Cl IIb-5 (5) —CH₂ OC₃H₇-i Cl IIb-6 (5) — CH₂ OC₄H₉-n Cl IIb-7 (5) — CH₂OCH(CH₃)C₅H₁₁-n Cl IIb-8 (5) (2) CH₂ OH Cl F IIb-9 (5) (2) CH₂ OH Cl ClIIb-10 (5) — CH₂ OCH₂CH═CH₂ Cl IIb-11 (5) — CH₂ OC₄H₉-i Cl IIb-12 (5) Cl— CH₂

IIb-13 (5) Cl —

OCH₂CH═CH₂ IIb-14 (5) Cl —

OC₂H₅ IIb-15 (5) Cl —

OCH₃

Examples of the compounds of the formula (IIc) which are veryparticularly preferred as herbicide safeners according to the inventionare listed in the table below.

TABLE Examples of the compounds of the formula (IIc) Example No. R¹⁶ N(R¹⁷, R¹⁸) IIc-1 CHCl₂ N(CH₂CH═CH₂)₂ IIc-2 CHCl₂

IIc-3 CHCl₂

IIc-4 CHCl₂

IIc-5 CHCl₂

IIc-6 CHCl₂

IIc-7 CHCl₂

Examples of the compounds of the formula (IId) which are veryparticularly preferred as herbicide safeners according to the inventionare listed in the table below.

TABLE Examples of the compounds of the formula (IId) Example (positions)(positions) No. R²² R²³ R²⁴ (X⁴)_(t) (X⁵)_(v) IId-1 H H CH₃ (2) OCH₃ —IId-2 H H C₂H₅ (2) OCH₃ — IId-3 H H C₃H₇-n (2) OCH₃ — IId-4 H H C₃H₇-i(2) OCH₃ — IId-5 H H

(2) OCH₃ IId-6 H H CH₃ (2) OCH₃ — (5) CH₃ IId-7 H H C₂H₅ (2) OCH₃ — (5)CH₃ IId-8 H H C₃H₇-n (2) OCH₃ — (5) CH₃ IId-9 H H C₃H₇-i (2) OCH₃ — (5)CH₃ IId-10 H H

(2) OCH₃ (5) CH₃ — IId-11 H H OCH₃ (2) OCH₃ — (5) CH₃ IId-12 H H OC₂H₅(2) OCH₃ — (5) CH₃ IId-13 H H OC₃H₇-i (2) OCH₃ — (5) CH₃ IId-14 H H SCH₃(2) OCH₃ — (5) CH₃ IId-15 H H SC₂H₅ (2) OCH₃ — (5) CH₃ IId-16 H HSC₃H₇-i (2) OCH₃ — (5) CH₃ IId-17 H H NHCH₃ (2) OCH₃ — (5) CH₃ IId-18 HH NHC₂H₅ (2) OCH₃ — (5) CH₃ IId-19 H H NHC₃H₇-i (2) OCH₃ — (5) CH₃IId-20 H H

(2) OCH₃ (5) CH₃ — IId-21 H H NHCH₃ (2) OCH₃ — IId-22 H H NHC₃H₇-i (2)OCH₃ — IId-23 H H N(CH₃)₂ (2) OCH₃ — IId-24 H H N(CH₃)₂ (3) CH₃ — (4)CH₃ IId-25 H H CH₂—O—CH₃ (2) OCH₃ —

Examples of the compounds of the formula (IIe) which are veryparticularly preferred as herbicide safeners according to the inventionare listed in the table below.

TABLE Examples of the compounds of the formula (IIe) Example (positions)(positions) No. R²² R²⁵ R²⁶ (X⁴)_(t) (X⁵)_(v) IIe-1 H H CH₃ (2) OCH₃ —IIe-2 H H C₂H₅ (2) OCH₃ — IIe-3 H H C₃H₇-n (2) OCH₃ — IIe-4 H H C₃H₇-i(2) OCH₃ — IIe-5 H H

(2) OCH₃ — IIe-6 H CH₃ CH₃ (2) OCH₃ — IIe-7 H H CH₃ (2) OCH₃ — (5) CH₃IIe-8 H H C₂H₅ (2) OCH₃ — (5) CH₃ IIe-9 H H C₃H₇-n (2) OCH₃ — (5) CH₃IIe-10 H H C₃H₇-i (2) OCH₃ — (5) CH₃ IIe-11 H H

(2) OCH₃ (5) CH₃ — IIe-12 H CH₃ CH₃ (2) OCH₃ — (5) CH₃

Most preferred as the crop plant tolerance promoter compound [component(b′)] are cloquintocetmexyl, fenchlorazole-ethyl, isoxadifen-ethyl,mefenpyr-diethyl, furilazole, fenclorim, cumyluron, dymron, dimepiperateand the compounds IIe-5 and IIe-11, and particular emphasis is given tocloquintocet-mexyl and mefenpyr-diethyl.

The compounds of the general formula (IIa) to be used as safenersaccording to the invention are known and/or can be prepared by processesknown per se (cf. WO-A-91/07874, WO-A-95/07897).

The compounds of the general formula (IIb) to be used as safenersaccording to the invention are known and/or can be prepared by processesknown per se (cf. EP-A-191736).

The compounds of the general formula (IIc) to be used as safenersaccording to the invention are known and/or can be prepared by processesknown per se (cf. DE-A-2218097, DE-A-2350547).

The compounds of the general formula (IId) to be used as safenersaccording to the invention are known and/or can be prepared by processesknown per se (cf. DE-A-19621522/U.S. Pat. No. 6,235,680).

The compounds of the general formula (IIe) to be used as safenersaccording to the invention are known and can be prepared by processesknown per se (cf. WO-A-99/66795/U.S. Pat. No. 6,251,827).

Examples of the selectively herbicidal combinations according to theinvention comprising in each case one active compound of the formula (I)and one of the safeners defined above are listed in the table below.

TABLE Examples of the combinations according to the invention Activecompounds of the formula (I) Safener I-a cloquintocet-mexyl I-afenchlorazole-ethyl I-a isoxadifen-ethyl I-a mefenpyr-diethyl I-afurilazole I-a fenclorim I-a cumyluron I-a daimuron/dymron I-adimepiperate I-a IIe-11 I-a IIe-5 I-b cloquintocet-mexyl I-bfenchlorazole-ethyl I-b isoxadifen-ethyl I-b mefenpyr-diethyl I-bfurilazole I-b fenclorim I-b cumyluron I-b daimuron/dymron I-bdimepiperate I-b IIe-11 I-b IIe-5 I-c cloquintocet-mexyl I-cfenchlorazole-ethyl I-c isoxadifen-ethyl I-c mefenpyr-diethyl I-cfurilazole I-c fenclorim I-c cumyluron I-c daimuron/dymron I-cdimepiperate I-c IIe-5 I-c IIe-11 I-d cloquintocet-mexyl I-dfenchlorazole-ethyl I-d isoxadifen-ethyl I-d mefenpyr-diethyl I-dfurilazole I-d fenclorim I-d cumyluron I-d daimuron/dymron I-ddimepiperate I-d IIe-11 I-d IIe-5 I-e cloquintocet-mexyl I-efenchlorazole-ethyl I-e isoxadifen-ethyl I-e mefenpyr-diethyl I-efurilazole I-e fenclorim I-e cumyluron I-e daimuron/dymron I-edimepiperate I-e IIe-5 I-e IIe-11 I-f cloquintocet-mexyl I-ffenchlorazole-ethyl I-f isoxadifen-ethyl I-f mefenpyr-diethyl I-ffurilazole I-f fenclorim I-f cumyluron I-f daimuron/dymron I-fdimepiperate I-f IIe-5 I-f IIe-11 I-g cloquintocet-mexyl I-gfenchlorazole-ethyl I-g isoxadifen-ethyl I-g mefenpyr-diethyl I-gfurilazole I-g fenclorim I-g cumyluron I-g daimuron/dymron I-gdimepiperate I-g IIe-5 I-g IIe-11

Surprisingly, it has now been found that the active compoundcombinations defined above of compounds of the general formula (I) andsafeners (antidotes) from the group (b′) set out above combine very goodutility plant tolerance with a particularly high herbicidal activity andcan be used in various crops, in particular in cereals (especiallywheat), but also in soya, potatoes, maize and rice, for the selectivecontrol of weeds.

In this context it is to be considered surprising that, from amultiplicity of known safeners or antidotes capable of antagonizing thedamaging effect of a herbicide on the crop plants, it is specificallythe compounds of group (b′) set out above which are suitable forcompensating—almost completely—the damaging effect of substituted cyclicketoenols on the crop plants, without at the same time having anycritical adverse effect on the herbicidal activity against the weeds.

Emphasis may be given here to the particularly advantageous effect ofthe particularly preferred and most preferred combination partners fromgroup (b′), in particular with regard to the gentle treatment of cerealplants, such as wheat, barley and rye, for example, but also maize andrice, as crop plants.

In the literature it has already been described how the action ofvarious active compounds can be boosted by addition of ammonium salts.The salts in question, however, are detersive salts (e.g. WO 95/017817)or salts which have relatively long alkyl substituents and/or arylsubstituents and which have a permeabilizing action or which increasethe active compound's solubility (e.g. EP-A 0 453 086, EP-A 0 664 081,FR-A 2 600 494, U.S. Pat. No. 4,844,734, U.S. Pat. No. 5,462,912, U.S.Pat. No. 5,538,937, US-A 03/0224939, US-A 05/0009880, US-A 05/0096386).Moreover, the prior art describes the action only for particular activecompounds and/or particular applications of the correspondingcompositions. In other cases, in turn, the salts in question are thoseof sulphonic acids, where the acids themselves have a paralytic actionon insects (U.S. Pat. No. 2,842,476). A boost to action by ammoniumsulphate, for example, is described by way of example for the herbicidesglyphosate and phosphinothricin (U.S. Pat. No. 6,645,914, EP-A2 0 036106). A corresponding action in the case of insecticides is neitherdisclosed nor suggested by this prior art.

The use of ammonium sulphate as a formulating assistant has also beendescribed for certain active compounds and applications (WO 92/16108),but its purpose therein is to stabilize the formulation, not to boostthe action.

It has now been found, entirely surprisingly, that the action ofinsecticides and/or acaricides and/or herbicides from the class of thealkoxyalkyl-substituted cyclic ketoenols can be boosted significantlythrough the addition of ammonium salts or phosphonium salts to theapplication solution or through the incorporation of these salts into aformulation comprising alkoxyalkyl-substituted cyclic ketoenols. Thepresent invention therefore provides for the use of ammonium salts orphosphonium salts for boosting the action of crop protectioncompositions which comprise as their active compound herbicidal and/orinsecticidal and/or acaricidal alkoxyalkyl-substituted cyclic ketoenols.The invention likewise provides compositions which comprise herbicidaland/or acaricidal and/or insecticidal alkoxyalkyl-substituted cyclicketoenols and action-boosting ammonium salts or phosphonium salts,including not only formulated active compounds but also ready-to-usecompositions (spray liquors). The invention further provides, finally,for the use of these compositions for controlling insect pests and/orspider mites and/or unwanted plant growth.

The compounds of the formula (I) possess a broad insecticidal and/oracaricidal and/or herbicidal activity, but individually the activityand/or plant tolerance leaves something to be desired.

The active compounds can be used in the compositions of the invention ina broad concentration range. The concentration of the active compoundsin the formulation is typically 0.1%-50% by weight.

Ammonium salts and phosphonium salts which inventively boost theactivity of crop protection compositions comprising fatty acidbiosynthesis inhibitors are defined by formula (III′)

in which

-   D represents nitrogen or phosphorus,-   D preferably represents nitrogen,-   R²⁶, R²⁷, R²⁸ and R²⁹ independently of one another represent    hydrogen or in each case optionally substituted C₁-C₈-alkyl or mono-    or polyunsaturated, optionally substituted C₁-C₈-alkylene, the    substituents being selectable from halogen, nitro and cyano,-   R²⁶, R²⁷, R²⁸ and R²⁹ independently of one another preferably    represent hydrogen or in each case optionally substituted    C₁-C₄-alkyl, the substituents being selectable from halogen, nitro    and cyano,-   R²⁶, R²⁷, R²⁸ and R²⁹ independently of one another particularly    preferably represent hydrogen, methyl, ethyl, n-propyl, isopropyl,    n-butyl, isobutyl, sec-butyl or tert-butyl,-   R²⁶, R²⁷, R²⁸ and R²⁹ very particularly preferably represent    hydrogen,-   n represents 1, 2, 3 or 4,-   n preferably represents 1 or 2,-   R³⁰ represents an organic or inorganic anion,-   R³⁰ preferably represents hydrogencarbonate, tetraborate, fluoride,    bromide, iodide, chloride, monohydrogenphosphate,    dihydrogenphosphate, hydrogensulphate, tartrate, sulphate, nitrate,    thiosulphate, thiocyanate, formate, lactate, acetate, propionate,    butyrate, pentanoate or oxalate,-   R³⁰ particularly preferably represents lactate, sulphate, nitrate,    thiosulphate, thiocyanate, oxalate or formate.-   R³⁰ very particularly preferably represents sulphate.

Inventively emphasized combinations of active compound, salt andpenetrant are listed in the table below. “Penetrant as per test” meanshere that any compound that acts as a penetrant in the cuticlepenetration test (Baur et al., 1997, Pesticide Science 51, 131-152) issuitable.

The ammonium salts and phosphonium salts of the formula (III′) can beused in a broad concentration range to boost the activity of cropprotection compositions comprising ketoenols. In general the ammoniumsalts or phosphonium salts are used in the ready-to-use crop protectioncomposition in a concentration of 0.5 to 80 mmol/l, preferably 0.75 to37.5 mmol/l, more preferably 1.5 to 25 mmol/l. In the case of aformulated product the ammonium salt and/or phosphonium saltconcentration in the formulation is chosen such that it is within thesestated general, preferred or particularly preferred ranges after theformulation has been diluted to the desired active-ingredientconcentration. The concentration of the salt in the formulation istypically 1%-50% by weight.

In one preferred embodiment of the invention the activity is boosted byadding to the crop protection compositions not only an ammonium saltand/or phosphonium salt but also, additionally, a penetrant. It isconsidered entirely surprising that even in these cases an even greaterboost to activity is observed. The present invention therefore likewiseprovides for the use of a combination of penetrant and ammonium saltsand/or phosphonium salts to boost the activity of crop protectioncompositions which comprise insecticidal, alkoxyalkyl-substituted cyclicketoenols as active compound. The invention likewise providescompositions which comprise herbicidal and/or acaricidal and/orinsecticidal alkoxyalkyl-substituted cyclic ketoenols, penetrants andammonium salts and/or phosphonium salts, including specifically not onlyformulated active compounds but also ready-to-use compositions (sprayliquors). The invention additionally provides, finally, for the use ofthese compositions for controlling insect pests.

Suitable penetrants in the present context include all those substanceswhich are typically used to enhance the penetration of activeagrochemical compounds into plants. Penetrants are defined in thiscontext by their ability to penetrate from the aqueous spray liquorand/or from the spray coating into the cuticle of the plant and therebyto increase the mobility of active compounds in the cuticle. The methoddescribed in the literature (Baur et al., 1997, Pesticide Science 51,131-152) can be used in order to determine this property.

Examples of suitable penetrants include alkanol alkoxylates. Penetrantsof the invention are alkanol alkoxylates of the formula (IV′)

R—O-(-AO)_(v)—R′  (IV′)

in which

-   -   R is linear or branched alkyl having 4 to 20 carbon atoms,    -   R′ is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl,        isobutyl, tert-butyl, n-pentyl or n-hexyl,    -   AO is an ethylene oxide radical, a propylene oxide radical, a        butylene oxide radical or is mixtures of ethylene oxide and        propylene oxide radicals or butylene oxide radicals, and    -   v is a number from 2 to 30.

One preferred group of penetrants are alkanol alkoxylates of the formula

R—O-(-EO—)_(n)—R′  (IV′-a)

in which

-   -   R is as defined above,    -   R′ is as defined above,    -   EO is —CH₂—CH₂—O—, and    -   n is a number from 2 to 20.

A further preferred group of penetrants are alkanol alkoxylates of theformula

R—O-(-EO—)_(p)—(—PO—)_(q)—R′  (IV′-b)

in which

-   -   R is as defined above,    -   R′ is as defined above,    -   EO is —CH₂—CH₂—O—,    -   PO is

-   -   p is a number from 1 to 10, and    -   q is a number from 1 to 10.

A further preferred group of penetrants are alkanol alkoxylates of theformula

R—O—(—PO—)_(r)-(EO—)_(s)—R′  (IV′-c)

in which

-   -   R is as defined above,    -   R′ is as defined above,    -   EO is —CH₂—CH₂—O—,    -   PO is

-   -   r is a number from 1 to 10, and    -   s is a number from 1 to 10.

A further preferred group of penetrants are alkanol alkoxylates of theformula

R—O-(-EO—)_(p)—(—BO—)_(q)—R′  (IV′-d)

in which

-   -   R and R′ are as defined above,    -   EO is CH₂—CH₂—O—,    -   BO is

-   -   p is a number from 1 to 10 and    -   q is a number from 1 to 10.

A further preferred group of penetrants are alkanol alkoxylates of theformula

R—O—(—BO-)_(r)-(-EO—)_(s)—R′  (IV′-e)

in which

-   -   R and R′ are as defined above,    -   BO is

-   -   EO is CH₂—CH₂—O—,    -   r is a number from 1 to 10 and    -   s is a number from 1 to 10.

A further preferred group of penetrants are alkanol alkoxylates of theformula

CH₃—(CH₂)_(t)—CH₂—O—(—CH₂—CH₂—O—)_(u)—R′  (IV′-f)

in which

-   -   R′ is as defined above,    -   t is a number from 8 to 13,    -   u is a number from 6 to 17.

In the formulae indicated above,

-   R is preferably butyl, isobutyl, n-pentyl, isopentyl, neopentyl,    n-hexyl, isohexyl, n-octyl, isooctyl, 2-ethylhexyl, nonyl, isononyl,    decyl, n-dodecyl, isododecyl, lauryl, myristyl, isotridecyl,    trimethylnonyl, palmityl, stearyl or eicosyl.

As an example of an alkanol alkoxylate of the formula (IV′-c) mentionmay be made of 2-ethylhexyl alkoxylate of the formula

in which

-   -   EO is —CH₂—CH₂—O—,    -   PO is

-   -    and        the numbers 8 and 6 represent average values.

As an example of an alkanol alkoxylate of the formula (IV′-d) mentionmay be made of the formula

CH₃—(CH₂)₁₀—O-(-EO—)₆—(—BO—)₂—CH₃  (IV′-d-1)

in which

-   -   EO is CH₂—CH₂—O—,    -   BO is

-   -    and    -   the numbers 10, 6 and 2 represent average values.

Particularly preferred alkanol alkoxylates of the formula (IV′-f) arecompounds of this formula in which

-   -   t is a number from 9 to 12 and    -   u is a number from 7 to 9.

Mention may be made with very particular preference of alkanolalkoxylate of the formula (IV′-f-1)

CH₃—(CH₂)_(t)—CH₂—O—(—CH₂—CH₂—O—)_(u)—H  (IV′-f-1)

in which

-   -   t stands for the average value 10.5 and    -   u stands for the average value 8.4.

A general definition of the alkanol alkoxylates is given by the formulaeabove. These substances are mixtures of compounds of the stated typewith different chain lengths. The indices therefore have average valueswhich may also deviate from whole numbers.

The alkanol alkoxylates of the formulae stated are known and in somecases are available commercially or can be prepared by known methods(cf. WO 98/35 553, WO 00/35 278 and EP-A 0 681 865).

Suitable penetrants also include, for example, substances which promotethe availability of the compounds of the formula (I) in the spraycoating. These include, for example, mineral or vegetable oils. Suitableoils are all mineral or vegetable oils—modified or otherwise—which cantypically be used in agrochemical compositions. Mention may be made byway of example of sunflower oil, rapeseed oil, olive oil, castor oil,colza oil, maize seed oil, cotton seed oil and soybean oil, or theesters of said oils. Preference is given to rapeseed oil, sunflower oiland their methyl or ethyl esters.

The concentration of penetrant in the compositions of the invention canbe varied within a wide range. In the case of a formulated cropprotection composition it is in general 1% to 95%, preferably 1% to 55%,more preferably 15%-40% by weight. In the ready-to-use compositions(spray liquors) the concentrations are generally between 0.1 and 10 g/l,preferably between 0.5 and g/l.

Crop protection compositions of the invention may also comprise furthercomponents, examples being surfactants and/or dispersing assistants oremulsifiers.

Suitable nonionic surfactants and/or dispersing assistants include allsubstances of this type that can typically be used in agrochemicalcompositions. Preferably mention may be made of polyethyleneoxide-polypropylene oxide block copolymers, polyethylene glycol ethersof linear alcohols, reaction products of fatty acids with ethylene oxideand/or propylene oxide, and also polyvinyl alcohol,polyvinylpyrrolidone, copolymers of polyvinyl alcohol andpolyvinylpyrrolidone, and copolymers of (meth)acrylic acid and(meth)acrylic esters, and additionally alkyl ethoxylates and alkylarylethoxylates, which optionally may be phosphated and optionally may beneutralized with bases, mention being made, by way of example, ofsorbitol ethoxylates, and, as well, polyoxyalkylenamine derivatives.

Suitable anionic surfactants include all substances of this type thatcan typically be used in agrochemical compositions. Preference is givento alkali metal salts and alkaline earth metal salts of alkylsulphonicacids or alkylarylsulphonic acids.

A further preferred group of anionic surfactants and/or dispersingassistants are the following salts that are of low solubility in plantoil: salts of polystyrenesulphonic acids, salts of polyvinylsulphonicacids, salts of naphthalenesulphonic acid-formaldehyde condensationproducts, salts of condensation products of naphthalenesulphonic acid,phenolsulphonic acid and formaldehyde, and salts of lignosulphonic acid.

Suitable additives which may be included in the formulations of theinvention are emulsifiers, foam inhibitors, preservatives, antioxidants,colorants and inert filling materials.

Preferred emulsifiers are ethoxylated nonylphenols, reaction products ofalkylphenols with ethylene oxide and/or propylene oxide, ethoxylatedarylalkylphenols, and also ethoxylated and propoxylatedarylalkylphenols, and also sulphated or phosphated arylalkyl ethoxylatesand/or arylalkyl ethoxypropoxylates, mention being made by way ofexample of sorbitan derivatives, such as polyethylene oxide-sorbitanfatty acid esters, and sorbitan fatty acid esters.

Using, for example, according to process (A), ethylN-[(4-(4-chlorophenyl)-2,6-dimethyl)-phenylacetyl]-2-amino-3-methoxy-2-methylpropionateas starting material, the course of the process of the invention can berepresented by the following reaction scheme:

Using, for example, according to process (Bα),3-[4-(4-chlorophenyl)-2,6-dimethylphenyl]-5-methoxymethyl-5-methylpyrrolidine-2,4-dioneand pivaloyl chloride as starting materials, the course of the processof the invention can be represented by the following reaction scheme:

Using, for example, according to process (B) (variant β),3-[5-(4-chlorophenyl)-2-chlorophenyl]-5-methoxymethyl-5-methylpyrrolidine-2,4-dioneand acetic anhydride as starting compounds, the course of the process ofthe invention can be represented by the following reaction scheme:

Using, for example, according to process (C),3-[4-(4-chlorophenyl)-[(2-chloro-6-methylphenyl]]-5-methoxyethyl-5-methylpyrrolidine-2,4-dioneand ethyl chloroformate as starting compounds, the course of the processof the invention can be represented by the following reaction scheme:

Using, for example, according to process (D),3-[4-(4-chlorophenyl)-2,6-dimethylphenyl]-1-oxa-spiro[4.5]decane-2,4-dioneand methyl chloromonothioformate as starting products, the course of thereaction can be represented as follows:

Using, for example, according to process (E),3-[3-(4-chlorophenyl)-2,6-dimethylphenyl]-5-methoxymethyl-5-methylpyrrolidine-2,4-dioneand methanesulphonyl chloride as starting product, the course of thereaction can be represented by the following reaction scheme:

Using, for example, according to process (F),3-[3-(4-chlorophenyl)-2,6-dimethylphenyl]-5-methoxymethyl-5-methylpyrrolidine-2,4-dioneand methanethiophosphonyl chloride 2,2,2-trifluoroethyl ester asstarting products, the course of the reaction can be represented by thefollowing reaction scheme:

Using, for example, according to process (G),3-[3-(4-chlorophenyl)-2,6-dimethylphenyl]-5-methoxyethyl-5-methylpyrrolidine-2,4-dioneand NaOH as components, the course of the process of the invention canbe represented by the following reaction scheme:

Using, for example, according to process (H) (variant α),3-[5-(4-chlorophenyl)-2-methylphenyl]-5-methoxymethyl-5-methylpyrrolidine-2,4-dioneand ethyl isocyanate as starting products, the course of the reactioncan be represented by the following reaction scheme:

Using, for example, according to process (H) (variant β),3-[3-(4-chlorophenyl)-2,6-dimethylphenyl]-5-methoxymethyl-5-methylpyrrolidine-2,4-dioneand dimethylcarbamoyl chloride as starting products, the course of thereaction can be represented by the following scheme:

Using, for example, according to process (Iβ),3-(4-bromo-2,6-dimethylphenyl)-5-methoxymethyl-5-methylpyrrolidine-2,4-dioneand 4-chlorophenylboronic acid as starting materials, the course of thereaction can be represented by the following scheme:

The compounds of the formula (II)

in whichA, B, D, W, X, Y, Z and R⁸ have the definitions indicated above,needed as starting materials for process (A) of the invention, are new.

The acylamino acid esters of the formula (II) are obtained, for example,if amino acid derivatives of the formula (XIII)

in whichA, B, D and R⁸ have the definition indicated above,are acylated with substituted phenylacetic acid derivatives of theformula (XIV)

in which

-   W, X, Y and Z have the definitions indicated above and-   U is a leaving group introduced by carboxylic acid activating    reagents such as carbonyldiimidazole, carbonyldiimides (such as, for    example, dicyclohexylcarbodiimide), phosphorylating reagents (such    as, for example, POCl₃, BOP-Cl), halogenating agents such as, for    example, thionyl chloride, oxalyl chloride, phosgene or chloroformic    esters,    (Chem. Reviews 52, 237416 (1953); Bhattacharya, Indian J. Chem. 6,    341-5, 1968)    or if acylamino acids of the formula (XV)

in whichA, B, D, W, X, Y and Z have the definitions indicated aboveare esterified (Chem. Ind. (London) 1568 (1968)).The compounds of the formula (XV)

in whichA, B, D, W, X, Y and Z have the definitions indicated aboveare new.

The compounds of the formula (XV) are obtained, for example, if1-aminocarboxylic acids of the formula (XVI)

in whichA, B and D have the definitions indicated aboveare acylated with substituted phenylacetic acid derivatives of theformula (XIV)

in whichU, W, X, Y and Z have the definitions indicated abovein accordance for example with Schotten-Baumann (Organikum, VEBDeutscher Verlag der Wissenschaften, Berlin 1977, p. 505).

The compounds of the formula (XIV) are in some cases known and/or can beprepared by the known processes in the laid-open specifications cited atthe outset.

The compounds of the formula (XIII) and (XVI) are in some cases new andcan be prepared by known processes (see, for example, Compagnon, Ann.Chim. (Paris) [14] 5, pp. 11-22, 23-27 (1970), L. Munday, J. Chem. Soc.4372 (1961); J. T. Eward, C. Jitrangeri, Can. J. Chem. 53, 3339 (1975)).

Furthermore, the starting materials of the formula (II)

in whichA, B, D, W, X, Y, Z and R⁸ have the definitions indicated above,used in process (A) above, can be prepared if 1-aminocarbonitriles ofthe formula (XVII)

in whichA, B and D have the definitions indicated above,are reacted with substituted phenylacetic acid derivatives of theformula (XIV)

in whichU, W, X, Y and Z have the definitions indicated aboveto give compounds of the formula (XVIII)

in whichA, B, D, W, X, Y and Z have the definitions indicated above,and these compounds are then subjected to acidic alcoholysis.

The compounds of the formula (XVI) are obtained, for example, byreacting hydantoins of the formula (XX)

in which A, B and D have the definitions indicated above.

The compounds of the formula (XX) are in some cases new and can beprepared by known processes.

The compounds of the formula (XVIII) are likewise new. The compounds ofthe formula (XVII) are in some cases new and can be prepared for exampleas described in EP-A-595 130.

The compounds I-a′ to I-g′ and I-a″ to I-g″ are in some cases describedin DE-A-06018828 or can be prepared by the processes described therein.

The acid halides of the formula (III), carboxylic anhydrides of theformula (IV), chloroformic esters or chloroformic thioesters of theformula (V), chloromonothioformic esters or chlorodithioformic esters ofthe formula (VI), sulphonyl chlorides of the formula (VII), phosphoruscompounds of the formula (VIII) and metal hydroxides, metal alkoxides oramines of the formula (IX) and (X) and isocyanates of the formula (XI)and carbamoyl chlorides of the formula (XII) and boronic acids of theformula (XIX), which are needed additionally as starting materials forcarrying out processes (B), (C), (D), (E), (F), (G), (H) and (I) of theinvention, are compounds which are general knowledge within organic orinorganic chemistry.

Process (A) is characterized in that compounds of the formula (II), inwhich A, B, D, W, X, Y, Z and R⁸ have the definitions indicated above,are subjected to intramolecular condensation in the presence of adiluent and in the presence of a base.

Diluents which can be used in process (A) of the invention include allorganic solvents that are inert towards the reactants. With preferenceit is possible to use hydrocarbons, such as toluene and xylene, andethers, such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethylether and diglycol dimethyl ether, additionally, polar solvents, such asdimethyl sulphoxide, sulpholane, dimethylformamide andN-methylpyrrolidone, and also alcohols such as methanol, ethanol,propanol, isopropanol, butanol, isobutanol and tert-butanol.

Bases (deprotonating agents) which can be used when carrying out process(A) of the invention include all typical proton acceptors. Withpreference it is possible to use alkali metal and alkaline earth metaloxides, hydroxides and carbonates, such as sodium hydroxide, potassiumhydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassiumcarbonate and calcium carbonate, which can also be used in the presenceof phase transfer catalysts such as triethylbenzylammonium chloride,tetrabutylammonium bromide, Adogen 464 (i.e.methyltrialkyl(C₈-C₁₀)ammonium chloride) or TDA 1 (i.e.tris(methoxyethoxyethyl)amine). In addition it is possible to use alkalimetals such as sodium or potassium. Others which may be employed arealkali metal and alkaline earth metal amides and hydrides, such assodium amide, sodium hydride and calcium hydride, and also alkali metalalkoxides, such as sodium methoxide, sodium ethoxide and potassiumtert-butoxide.

The reaction temperature when carrying out process (A) of the inventionmay be varied within a relatively wide range. Generally it is operatedat temperatures between −75° C. and 200° C., preferably between −50° C.and 150° C.

Process (A) of the invention is generally carried out under atmosphericpressure.

When process (A) of the invention is being carried out, the reactioncomponent of the formula (II) and the deprotonating base are generallyused in equimolar to approximately twice-equimolar amounts. It is alsopossible, however, to use one or the other component in a larger excess(up to 3 mol).

Process (B_(α)) is characterized in that compounds of the formula (I-a)are reacted in each case with carbonyl halides of the formula (III),optionally in the presence of a diluent and optionally in the presenceof an acid-binding agent.

Diluents which can be used in process (B_(α)) of the invention includeall solvents that are inert towards the acid halides. With preference itis possible to use hydrocarbons, such as benzine, benzene, toluene,xylene and tetralin, and halogenated hydrocarbons, such as methylenechloride, chloroform, carbon tetrachloride, chlorobenzene ando-dichlorobenzene, and ketones, such as acetone and methyl isopropylketone, and ethers, such as diethyl ether, tetrahydrofuran and dioxane,and carboxylic esters, such as ethyl acetate, and also strongly polarsolvents, such as dimethylformamide, dimethyl sulphoxide and sulpholane.If the stability of the acid halide to hydrolysis permits it, thereaction can also be carried out in the presence of water. Suitableacid-binding agents in the context of the reaction according to process(B_(α)) of the invention include all typical acid acceptors. Withpreference it is possible to use tertiary amines, such as triethylamine,pyridine, diazabicyclooctane (DABCO), diazabicycloundecene (DBU),diazabicyclononene (DBN), Hünig base and N,N-dimethylaniline, andalkaline earth metal oxides, such as magnesium oxide and calcium oxide,and alkali metal and alkaline earth metal carbonates, such as sodiumcarbonate, potassium carbonate and calcium carbonate, and also alkalimetal hydroxides such as sodium hydroxide and potassium hydroxide.

The reaction temperature for process (B_(α)) of the invention may bevaried within a relatively wide range. It is operated generally attemperatures between −20° C. and +150° C., preferably between 0° C. and100° C.

When process (B_(α)) of the invention is being carried out, the startingmaterials of the formula (I-a) and the carbonyl halide of the formula(III) are used generally in each case in approximately equivalentamounts. It is also possible, however, to use the carbonyl halide in alarger excess (up to 5 mol). Working up takes place in accordance withtypical methods.

Process (B_(β)) is characterized in that compounds of the formula (I-a)are reacted in each case with carboxylic anhydrides of the formula (IV),optionally in the presence of a diluent and optionally in the presenceof an acid-binding agent.

Diluents which can be used in process (B_(β)) of the invention arepreferably those diluents also contemplated with preference when usingacid halides. Moreover, it is also possible for a carboxylic anhydrideemployed in excess to function simultaneously as diluent.

Suitable acid-binding agents added optionally in process (B_(β)) arepreferably those acid-binding agents which are also suitable withpreference when using acid halides.

The reaction temperature in process (B_(β)) of the invention can bevaried within a relatively wide range. In general it is operated attemperatures between −20° C. and +150° C., preferably between 0° C. and100° C.

When process (B_(β)) of the invention is being carried out, the startingmaterials of the formulae (I-a) and the carboxylic anhydride of theformula (IV) are generally used in amounts which in each case areapproximately equivalent. It is also possible, however, to use thecarboxylic anhydride in a larger excess (up to 5 mol). Working up takesplace in accordance with typical methods.

A general procedure is to remove diluents and carboxylic anhydridepresent in excess, and also the resultant carboxylic acid, bydistillation or by washing with an organic solvent or with water.

Process (C) is characterized in that compounds of the formula (I-a) arereacted in each case with chloroformic esters or chloroformic thioestersof the formula (V), optionally in the presence of a diluent andoptionally in the presence of an acid-binding agent.

Suitable acid-binding agents for process (C) of the invention includeall typical acid acceptors. With preference it is possible to usetertiary amines, such as triethylamine, pyridine, DABCO, DBU, DBN, Hünigbase and N,N-dimethylaniline, and alkaline earth metal oxides, such asmagnesium oxide and calcium oxide, and alkali metal and alkaline earthmetal carbonates, such as sodium carbonate, potassium carbonate andcalcium carbonate, and also alkali metal hydroxides such as sodiumhydroxide and potassium hydroxide.

Diluents which can be used in process (C) of the invention include allsolvents that are inert towards the chloroformic esters and/orchloroformic thioesters. With preference it is possible to usehydrocarbons, such as benzine, benzene, toluene, xylene and tetralin,and halogenated hydrocarbons, such as methylene chloride, chloroform,carbon tetrachloride, chlorobenzene and o-dichlorobenzene, and ketones,such as acetone and methyl isopropyl ketone, and ethers, such as diethylether, tetrahydrofuran and dioxane, and carboxylic esters, such as ethylacetate, and nitriles such as acetonitrile, and also strongly polarsolvents, such as dimethylformamide, dimethyl sulphoxide and sulpholane.

The reaction temperature when carrying out process (C) of the inventioncan be varied within a relatively wide range. The reaction temperatureis generally between −20° C. and +100° C., preferably between 0° C. and50° C.

Process (C) of the invention is generally carried out under atmosphericpressure.

When process (C) of the invention is being carried out, the startingmaterials of the formula (I-a) and the corresponding chloroformic esterand/or chloroformic thioester of the formula (V) are used generally ineach case in approximately equivalent amounts. It is also possible,however, to use one or the other component in a larger excess (up to 2mol). Working up takes place in accordance with typical methods. Thegeneral procedure is to remove salts that have precipitated and toconcentrate the remaining reaction mixture by stripping off the diluent.

Process (D) of the invention is characterized in that compounds of theformula (I-a) are reacted in each case with compounds of the formula(VI) in the presence of a diluent and optionally in the presence of anacid-binding agent.

In preparation process (D) about 1 mol of chloromonothioformic esterand/or chlorodithioformic ester of the formula (VI) per mole of startingcompound of the formula (I-a) is reacted at 0 to 120° C., preferably at20 to 60° C.

Suitable diluents added optionally include all inert polar organicsolvents, such as ethers, amides, sulphones, sulphoxides, but alsohaloalkanes.

Preference is given to using dimethyl sulphoxide, tetrahydrofuran,dimethylformamide, ethyl acetate or methylene chloride.

If, in one preferred embodiment, the enolate salt of the compounds (I-a)is prepared, by the addition of strong deprotonating agents such assodium hydride or potassium tert-butoxide for example, it is possible toforego the further addition of acid-binding agents.

Bases which can be used in process (D) are all typical proton acceptors.With preference it is possible to use alkali metal hydrides, alkalimetal alkoxides, alkali metal or alkaline earth metal carbonates orhydrogen carbonates or nitrogen bases. By way of example mention may bemade of sodium hydride, sodium methoxide, sodium hydroxide, calciumhydroxide, potassium carbonate, sodium hydrogen carbonate,triethylamine, dibenzylamine, diisopropylamine, pyridine, quinoline,diazabicyclooctane (DABCO), diazabicyclononene (DBN) anddiazabicycloundecene (DBU).

The reaction can be carried out at atmospheric pressure or at anelevated pressure, but preferably at atmospheric pressure. Working uptakes place in accordance with typical methods.

Process (E) of the invention is characterized in that compounds of theformula (I-a) are reacted in each case with sulphonyl chlorides of theformula (VII), optionally in the presence of a diluent and optionally inthe presence of an acid-binding agent.

In preparation process (E) about 1 mol of sulphonyl chloride of theformula (VII) per mole of starting compound of the formula (I-a) isreacted at −20 to 150° C., preferably at 0 to 70° C.

Process (E) is carried out preferably in the presence of a diluent.

Suitable diluents include all inert polar organic solvents, such asethers, amides, ketones, carboxylic esters, nitrites, sulphones,sulphoxides or halogenated hydrocarbons such as methylene chloride.

Preference is given to using dimethyl sulphoxide, tetrahydrofuran,dimethylformamide, ethyl acetate or methylene chloride.

If, in one preferred embodiment, the enolate salt of the compound (I-a)is prepared, as a result of the addition of strong deprotonating agents(such as sodium hydride or potassium tert-butoxide, for example), thenit is possible to forego the further addition of acid-binding agents.

Where acid-binding agents are used, those suitable include typicalorganic or inorganic bases; by way of example, mention may be made ofsodium hydroxide, sodium carbonate, potassium carbonate, pyridine andtriethylamine.

The reaction can be carried out at atmospheric pressure or at anelevated pressure, but preferably at atmospheric pressure. Working uptakes place in accordance with typical methods.

Process (F) of the invention is characterized in that compounds of theformula (I-a) are reacted in each case with phosphorus compounds of theformula (VIII), optionally in the presence of a diluent and optionallyin the presence of an acid-binding agent.

In preparation process (F) compounds of the formula (I-e) are obtainedby reacting 1 to 2, preferably 1 to 1.3 mol of the phosphorus compoundof the formula (VIII) per mole of the compounds (I-a) at temperaturesbetween −40° C. and 150° C., preferably between −10 and 110° C.

Process (F) is carried out preferably in the presence of a diluent.

Suitable diluents include all inert, polar organic solvents, such asethers, carboxylic esters, halogenated hydrocarbons, ketones, amides,nitriles, sulphones, sulphoxides, etc.

Preference is given to using acetonitrile, dimethyl sulphoxide,tetrahydrofuran, dimethylformamide or methylene chloride.

Acid-binding agents, added optionally, suitably include typical organicor inorganic bases, such as hydroxides, carbonates or amines. Thosewhich may be recited by way of example include sodium hydroxide, sodiumcarbonate, potassium carbonate, pyridine and triethylamine.

The reaction can be carried out at atmospheric pressure or at anelevated pressure, but preferably at atmospheric pressure. Working uptakes place in accordance with typical methods of organic chemistry. Theend products are preferably purified by crystallization, bychromatographic purification or by partial distillation, i.e. removal ofthe volatile constituents in vacuo.

Process (G) is characterized in that compounds of the formula (I-a) arereacted in each case with metal hydroxides and/or metal alkoxides of theformula (IX) or amines of the formula (X), optionally in the presence ofa diluent.

Diluents which can be used in process (G) of the invention arepreferably ethers such as tetrahydrofuran, dioxane or diethyl ether orelse alcohols such as methanol, ethanol or isopropanol, but also water.Process (G) of the invention is carried out generally under atmosphericpressure. The reaction temperature is generally between −20° C. and 100°C., preferably between 0° C. and 50° C.

Process (H) of the invention is characterized in that compounds of theformula (I-a) are reacted in each case with (Hα) compounds of theformula (XI), optionally in the presence of a diluent and optionally inthe presence of a catalyst, or (Hβ) with compounds of the formula (XII),optionally in the presence of a diluent and optionally in the presenceof an acid-binding agent.

In preparation process (Hα) about 1 mol of isocyanate of the formula(XI) per mole of starting compound of the formula (I-a) is reacted at 0to 100° C., preferably at 20 to 50° C.

Process (Hα) is carried out preferably in the presence of a diluent.

Suitable diluents include all inert organic solvents, such as aromatichydrocarbons, halogenated hydrocarbons, ethers, amides, nitrites,sulphones or sulphoxides.

Optionally it is possible to add catalysts in order to accelerate thereaction. Catalysts which can be used to good advantage includeorganotin compounds, such as dibutyltin dilaurate, for example.

Operation takes place preferably under atmospheric pressure.

In preparation process (Hβ) about 1 mol of carbamoyl chloride of theformula (XII) per mole of starting compound of the formula (I-a) isreacted at 0 to 150° C., preferably at 20 to 70° C.

Suitable diluents, added optionally, include all inert polar organicsolvents, such as ethers, carboxylic esters, nitrites, ketones, amides,sulphones, sulphoxides or halogenated hydrocarbons.

Preference is given to using dimethyl sulphoxide, tetrahydrofuran,dimethylformamide or methylene chloride.

If, in one preferred embodiment, the enolate salt of the compound (I-a)is prepared, by the addition of strong deprotonating agents (such assodium hydride or potassium tert-butoxide, for example), it is possibleto forego the further addition of acid-binding agents.

If acid-binding agents are used, they suitably include typical organicor inorganic bases. By way of example, mention may be made of sodiumhydroxide, sodium carbonate, potassium carbonate, triethylamine orpyridine.

The reaction can be carried out at atmospheric pressure or at anelevated pressure, preferably at atmospheric pressure. Working up takesplace in accordance with typical methods.

For the implementation of process (Iα) and (Iβ) of the invention,palladium(0) complexes are suitable catalysts. Preference is given, forexample, to tetrakis(triphenylphosphine)palladium. Optionally it is alsopossible to use palladium(II) compounds, examples being PdCl₂, Pd(OAc)₂.When palladium(II) compounds are used, phosphines, such astricyclohexylphosphine, for example, are generally employed ascomplexing agents.

Suitable acid acceptors for the implementation of process (Iα) and (Iβ)of the invention are organic or inorganic bases. These include,preferably, alkaline earth metal or alkali metal hydroxides, acetates,carbonates or hydrogen carbonates, such as sodium, potassium, barium orammonium hydroxide, sodium, potassium, calcium or ammonium acetate,sodium, potassium, caesium or ammonium carbonate, sodium hydrogencarbonate or potassium hydrogen carbonate, for example, alkali metalfluorides, such as caesium fluoride, alkali metal phosphates such aspotassium dihydrogen phosphate, potassium phosphate, and also tertiaryamines, such as trimethylamine, triethylamine, tributylamine,N,N-dimethylaniline, N,N-dimethylbenzylamine, pyridine,N-methylpiperidine, N-methylmorpholine, N,N-dimethylaminopyridine,diazabicyclooctane (DABCO), diazabicyclononene (DBN) ordiazabicycloundecene (DBU).

Suitable diluents for implementing process (Iα) and (Iβ) of theinvention include water, organic solvents and any desired mixturesthereof. By way of example mention may be made of the following:aliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether,hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene,xylene or decalin, for example; halogenated hydrocarbons, such aschlorobenzene, dichlorobenzene, methylene chloride, chloroform,tetrachloromethane, dichloroethane, trichloroethane ortetrachloroethylene, for example; ethers, such as diethyl ether,diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether,dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane,diethylene glycol dimethyl ether or anisole; alcohols, such as methanol,ethanol, n- or i-propanol, n-, iso-, sec- or tert-butanol, ethanediol,propane-1,2-diol, ethoxyethanol, methoxyethanol, diethylene glycolmonomethyl ether, diethyl glycol monomethyl ether; water.

The reaction temperature in process (Iα) and (Iβ) of the invention canbe varied within a relatively wide range. Operation takes place ingeneral at temperatures between 0° C. and +140° C., preferably between50° C. and +100° C.

When process (Iα) and (Iβ) of the invention is being carried out, theboronic acids of the formulae (XIXα) and (XIXβ) in which Y and Z are asdefined above, and compounds of the formulae (I-a′) to (I-g′) in whichA, B, D, G, W, X, Y, and Z′, and (I-a″) to (I-g″) in which A, B, D, G,W, X, Z and Y′, are as defined above, are used in a molar ratio of 1:1to 3:1, preferably 1:1 to 2:1. The amount of catalyst used is generally0.005 to 0.5 mol, preferably 0.01 mol to 0.1 mol, per mole of thecompounds of the formulae (I-a′) to (I-g′) or (I-a″) to (I-g″). The baseis generally employed in an excess.

The inventive active compounds/active compound combinations, incombination with good plant tolerance and favourable toxicity towarm-blooded animals and being tolerated well by the environment, aresuitable for protecting plants and plant organs, for increasing theharvest yields, for improving the quality of the harvested material andfor controlling animal pests, in particular insects, arachnids,helminths, nematodes and molluscs, which are encountered in agriculture,in horticulture, in animal husbandry, in forests, in gardens and leisurefacilities, in the protection of stored products and of materials, andin the hygiene sector. They may be preferably employed as cropprotection compositions. They are active against normally sensitive andresistant species and against all or some stages of development. Theabovementioned pests include:

From the order of the Anoplura (Phthiraptera), for example, Damaliniaspp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectesspp.

From the class of the Arachnida, for example, Acarus siro, Aceriasheldoni, Aculops spp., Aculus spp., Amblyomma spp., Argas spp.,Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Chorioptes spp.,Dermanyssus gallinae, Eotetranychus spp., Epitrimerus pyri,Eutetranychus spp., Eriophyes spp., Hemitarsonemus spp., Hyalomma spp.,Ixodes spp., Latrodectus mactans, Metatetranychus spp., Oligonychusspp., Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora,Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp.,Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp.,Tarsonemus spp., Tetranychus spp., Vasates lycopersici.

From the class of the Bivalva, for example, Dreissena spp.

From the order of the Chilopoda, for example, Geophilus spp., Scutigeraspp.

From the order of the Coleoptera, for example, Acanthoscelides obtectus,Adoretus spp., Agelastica alni, Agriotes spp., Amphimallon solstitialis,Anobium punctatum, Anoplophora spp., Anthonomus spp., Anthrenus spp.,Apogonia spp., Atomaria spp., Aftagenus spp., Bruchidius obtectus,Bruchus spp., Ceuthorhynchus spp., Cleonus mendicus, Conoderus spp.,Cosmopolites spp., Costelytra zea-landica, Curculio spp., Cryptorhynchuslapathi, Dermestes spp., Diabrotica spp., Epilachna spp., Faustinuscubae, Gibbium psylloides, Heteronychus arator, Hylamorpha elegans,Hylotrupes bajulus, Hypera postica, Hypothenemus spp., Lachnostemaconsanguinea, Leptinotarsa decemlineata, Lissorhoptrus oryzophilus,Lixus spp., Lyctus spp., Meligethes aeneus, Melolontha melolontha,Migdolus spp., Monochamus spp., Naupactus xanthographus, Niptushololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Otiorrhynchussulcatus, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp.,Popillia japonica, Premnotrypes spp., Psylliodes chryso-cephala, Ptinusspp., Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp.,Sphenophorus spp., Sternechus spp., Symphyletes spp., Tenebrio molitor,Tribolium spp., Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrusspp.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Diptera, for example, Aedes spp., Anopheles spp.,Bibio hortulanus, Calliphora erythrocephala, Ceratitis capitata,Chrysomyia spp., Cochliomyia spp., Cordylobia anthropophaga, Culex spp.,Cuterebra spp., Dacus oleae, Dermatobia hominis, Drosophila spp., Fanniaspp., Gastrophilus spp., Hylemyia spp., Hyppobosca spp., Hypoderma spp.,Liriomyza spp., Lucilia spp., Musca spp., Nezara spp., Oestrus spp.,Oscinella frit, Pegomyia hyoscyami, Phorbia spp., Stomoxys spp., Tabanusspp., Tannia spp., Tipula paludosa.

From the class of the Gastropoda, for example, Arion spp., Biomphalariaspp., Bulinus spp., Deroceras spp., Galba spp., Lyrnaea spp.,Oncomelania spp., Succinea spp.

From the class of the helminths, for example, Ancylostoma duodenale,Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp.,Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori,Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp.,Dicrocoelium spp, Dictyocaulus filaria, Diphyllobothrium latum,Dracunculus medinensis, Echinococcus granulosus, Echinococcusmultilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp.,Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa,Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocercavolvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp,Strongyloides fuellebomi, Strongyloides stercoralis, Stronyloides spp.,Taenia saginata, Taenia solium, Trichinella spiralis, Trichinellanativa, Trichinella britovi, Trichinella nelsoni, Trichinellapseudopsiralis, Trichostrongulus spp., Trichuris trichuria, Wuchereriabancrofti.

It is furthermore possible to control Protozoa, such as Eimeria.

From the order of the Heteroptera, for example, Anasa tristis,Antestiopsis spp., Blissus spp., Calocoris spp., Campylomma livida,Cavelerius spp., Cimex spp., Creontiades dilutus, Dasynus piperis,Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistusspp., Eurygaster spp., Heliopeltis spp., Horcias nobilellus, Leptocorisaspp., Leptoglossus phyllopus, Lygus spp., Macropes excavatus, Miridae,Nezara spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp.,Psallus seriatus, Pseudacysta persea, Rhodnius spp., Sahlbergellasingularis, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatomaspp.

From the order of the Homoptera, for example, Acyrthosipon spp.,Aeneolamia spp., Agonoscena spp., Aleurodes spp., Aleurolobusbarodensis, Aleurothrixus spp., Amrasca spp., Anuraphis cardui,Aonidiella spp., Aphanostigma piri, Aphis spp., Arboridia apicalis,Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacorthum solani,Bemisia spp., Brachycaudus helichrysii, Brachycolus spp., Brevicorynebrassicae, Calligypona marginata, Cameocephala fulgida, Ceratovacunalanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii,Chionaspis tegalensis, Chlorita onukii, Chromaphis juglandicola,Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp.,Cryptomyzus ribis, Dalbulus spp., Dialeurodes spp., Diaphorina spp.,Diaspis spp., Drosicha spp., Dysaphis spp., Dysmicoccus spp., Empoascaspp., Eriosoma spp., Erythroneura spp., Euscelis bilobatus, Geococcuscoffeae, Homalodisca coagulata, Hyalopterus arundinis, Icerya spp.,Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp.,Lepidosaphes spp., Lipaphis erysimi, Macrosiphum spp., Mahanarvafimbriolata, Melanaphis sacchari, Metcalfiella spp., Metopolophiumdirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., Nasonoviaribisnigri, Nephotettix spp., Nilaparvata lugens, Oncometopia spp.,Orthezia praelonga, Parabemisia myricae, Paratrioza spp., Parlatoriaspp., Pemphigus spp., Peregrinus maidis, Phenacoccus spp., Phloeomyzuspasserinii, Phorodon humuli, Phylloxera spp., Pinnaspis aspidistrae,Planococcus spp., Protopulvinaria pyriformis, Pseudaulacaspis pentagona,Pseudococcus spp., Psylla spp., Pteromalus spp., Pyrilla spp.,Quadraspidiotus spp., Quesada gigas, Rastrococcus spp., Rhopalosiphumspp., Saissetia spp., Scaphoides titanus, Schizaphis graminum,Selenaspidus articulatus, Sogata spp., Sogatella furcifera, Sogatodesspp., Stictocephala festina, Tenalaphara malayensis, Tinocalliscaryaefoliae, Tomaspis spp., Toxoptera spp., Trialeurodes vaporariorum,Trioza spp., Typhlocyba spp., Unaspis spp., Viteus vitifolii.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampaspp., Lasius spp., Monomorium pharaonis, Vespa spp.

From the order of the Isopoda, for example, Armadillidium vulgare,Oniscus asellus, Porcellio scaber.

From the order of the Isoptera, for example, Reticulitermes spp.

From the order of the Lepidoptera, for example, Acronicta major, Aedialeucomelas, Agrotis spp., Alabama argillacea, Anticarsia spp., Barathrabrassicae, Bucculatrix thurberiella, Bupalus piniarius, Cacoecia podana,Capua reticulana, Carpocapsa pomonella, Chematobia brumata, Chilo spp.,Choristoneura fumiferana, Clysia ambiguella, Cnaphalocerus spp., Eariasinsulana, Ephestia kaehniella, Euproctis chrysorrhoea, Euxoa spp.,Feltia spp., Galleria mellonella, Helicoverpa spp., Heliothis spp.,Hofmannophila pseudospretella, Homona magnanima, Hyponomeuta padella,Laphygma spp., Lithocolletis blancardella, Lithophane antennata,Loxagrotis albicosta, Lymantria spp., Malacosoma neustria, Mamestrabrassicae, Mocis repanda, Mythimna separata, Oria spp., Oulema oryzae,Panolis flammea, Pectinophora gossypiella, Phyllocnistis citrella,Pieris spp., Plutella xylostella, Prodenia spp., Pseudaletia spp.,Pseudoplusia includens, Pyrausta nubilalis, Spodoptera spp., Thermesiagemmatalis, Tinea pellionella, Tineola bisselliella, Tortrix viridana,Trichoplusia spp.

From the order of the Orthoptera, for example, Acheta domesticus, Blattaorientalis, Blattella germanica, Gryllotalpa spp., Leucophaea maderae,Locusta spp., Melanoplus spp., Periplaneta americana, Schistocercagregaria.

From the order of the Siphonaptera, for example, Ceratophyllus spp.,Xenopsylla cheopis.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanoptera, for example, Baliothrips biformis,Ermeothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothripsfemoralis, Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothripscardamoni, Thrips spp.

From the order of the Thysanura, for example, Lepisma saccharina.

The phytoparasitic nematodes include, for example, Aphelenchoides spp.,Bursaphelenchus spp., Ditylenchus dipsaci, Globodera spp., Heteroderaspp., Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholussimilis, Trichodorus spp., Tylenchulus semipenetrans, Xiphinema spp.

If appropriate, the compounds/active compound combinations according tothe invention can, at certain concentrations or application rates, alsobe used as herbicides, safeners, growth regulators or agents to improveplant properties, or as microbicides, for example as fungicides,antimycotics, bactericides, viricides (including agents against viroids)or as agents against MLO (Mycoplasma-like organisms) and RLO(Rickettsia-like organisms). If appropriate, they can also be employedas intermediates or precursors for the synthesis of other activecompounds.

All plants and plant parts can be treated in accordance with theinvention. Plants are to be understood as meaning in the present contextall plants and plant populations such as desired and undesired wildplants or crop plants (including naturally occurring crop plants). Cropplants can be plants which can be obtained by conventional plantbreeding and optimization methods or by biotechnological and geneticengineering methods or by combinations of these methods, including thetransgenic plants and including the plant cultivars protectable or notprotectable by plant breeders' rights. Plant parts are to be understoodas meaning all parts and organs of plants above and below the ground,such as shoot, leaf, flower and root, examples which may be mentionedbeing leaves, needles, stalks, stems, flowers, fruit bodies, fruits andseeds, and also roots, tubers and rhizomes. The plant parts also includeharvested material, and vegetative and generative propagation material,for example cuttings, tubers, rhizomes, offshoots and seeds.

Treatment according to the invention of the plants and plant parts withthe active compounds/active compound combinations is carried outdirectly or by allowing the compounds to act on their surroundings,habitat or storage space by the customary treatment methods, for exampleby immersion, spraying, evaporation, fogging, scattering, painting on,injection and, in the case of propagation material, in particular in thecase of seeds, also by applying one or more coats.

The active compounds/active compound combinations can be converted tothe customary formulations, such as solutions, emulsions, wettablepowders, water- and oil-based suspensions, powders, dusting agents,pastes, soluble powders, soluble granules, granules for broadcasting,suspoemulsion concentrates, natural materials impregnated with activecompound, synthetic materials impregnated with active compound,fertilizers and microencapsulations in polymeric substances.

These formulations are produced in a known manner, for example by mixingthe active compounds/active compound combinations with extenders, thatis liquid solvents and/or solid carriers, optionally with the use ofsurface-active agents, that is emulsifiers and/or dispersants and/orfoam formers.

If the extender used is water, it is also possible to use organicsolvents, for example, as auxiliary solvents. Suitable liquid solventsare essentially: aromatics, such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics and chlorinated aliphatichydrocarbons, such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, forexample petroleum fractions, mineral and vegetable oils, alcohols, suchas butanol or glycol, as well as their ethers and esters, ketones, suchas acetone, methyl ethyl ketone, methyl isobutyl ketone orcyclohexanone, strongly polar solvents, such as dimethyl sulphoxide, andalso water.

Suitable solid carriers are:

for example ammonium salts and ground natural minerals such as kaolins,clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceousearth, and ground synthetic minerals such as highly disperse silica,alumina and silicates; suitable solid carriers for granules are: forexample crushed and fractionated natural rocks such as calcite, marble,pumice, sepiolite and dolomite, or else synthetic granules of inorganicand organic meals, and granules of organic material such as sawdust,coconut shells, maize cobs and tobacco stalks; suitable emulsifiersand/or foam formers are: for example nonionic and anionic emulsifierssuch as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcoholethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates, or else protein hydrolysates; suitabledispersants are: for example lignosulphite waste liquors andmethylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, or else naturalphospholipids such as cephalins and lecithins and syntheticphospholipids can be used in the formulations. Other additives can bemineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian blue, and organic colorants suchas alizarin colorants, azo colorants and metal phthalocyanine colorants,and trace nutrients such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95% by weight ofactive compound, preferably between 0.5 and 90%.

The active compound/active compound combinations according to theinvention can be present in their commercially available formulations,as well as in the use forms prepared from these formulations, in amixture with other active compounds such as insecticides, attractants,sterilizers, bactericides, acaricides, nematicides, fungicides,growth-regulating substances, herbicides, safeners, fertilizers orsemiochemicals.

Compounds which are particularly favourable as mixing partners are, forexample, the following:

Fungicides:

2-phenylphenol; 8-hydroxyquinoline sulphate; acibenzolar-5-methyl;aldimorph; amidoflumet; ampropylfos; ampropylfos-potassium; andoprim;anilazine; azaconazole; azoxystrobin; benalaxyl; benodanil; benomyl;benthiavalicarb-isopropyl; benzamacril; benzamacril-isobutyl; bilanafos;binapacryl; biphenyl; bitertanol; blasticidin-S; bromuconazole;bupirimate; buthiobate; butylamine; calcium polysulphide; capsimycin;captafol; captan; carbendazim; carboxin; carpropamid; carvone;chinomethionat; chlobenthiazone; chlorfenazole; chloroneb;chlorothalonil; chlozolinate; clozylacon; cyazofamid; cyflufenamid;cymoxanil; cyproconazole; cyprodinil; cyprofuram; Dagger G; debacarb;dichlofluanid; dichlone; dichlorophen; diclocymet; diclomezine;dicloran; diethofencarb; difenoconazole; diflumetorim; dimethirimol;dimethomorph; dimoxystrobin; diniconazole; diniconazole-M; dinocap;diphenylamine; dipyrithione; ditalimfos; dithianon; dodine; drazoxolon;edifenphos; epoxiconazole; ethaboxam; ethirimol; etridiazole;famoxadone; fenamidone; fenapanil; fenarimol; fenbuconazole; fenfuram;fenhexamid; fenitropan; fenoxanil; fenpiclonil; fenpropidin;fenpropimorph; ferbam; fluazinam; flubenzimine; fludioxonil; flumetover;flumorph; fluoromide; fluoxastrobin; fluquinconazole; flurprimidol;flusilazole; flusulfamide; flutolanil; flutriafol; folpet; fosetyl-Al;fosetyl-sodium; fuberidazole; furalaxyl; furametpyr; furcarbanil;furmecyclox; guazatine; hexachlorobenzene; hexaconazole; hymexazole;imazalil; imibenconazole; iminoctadine triacetate; iminoctadinetris(albesilate); iodocarb; ipconazole; iprobenfos; iprodione;iprovalicarb; irumamycin; isoprothiolane; isovaledione; kasugamycin;kresoxim-methyl; mancozeb; maneb; meferimzone; mepanipyrim; mepronil;metalaxyl; metalaxyl-M; metconazole; methasulfocarb; methfuroxam;metiram; metominostrobin; metsulfovax; mildiomycin; myclobutanil;myclozolin; natamycin; nicobifen; nitrothal-isopropyl; noviflumuron;nuarimol; ofurace; orysastrobin; oxadixyl; oxolinic acid; oxpoconazole;oxycarboxin; oxyfenthiin; paclobutrazole; pefurazoate; penconazole;pencycuron; phosdiphen; phthalide; picoxystrobin; piperalin; polyoxins;polyoxorim; probenazole; prochloraz; procymidone; propamocarb;propanosine-sodium; propiconazole; propineb; proquinazid;prothioconazole; pyraclostrobin; pyrazophos; pyrifenox; pyrimethanil;pyroquilon; pyroxyfur; pyrrolenitrine; quinconazole; quinoxyfen;quintozene; simeconazole; spiroxamine; sulphur; tebuconazole;tecloftalam; tecnazene; tetcyclacis; tetraconazole; thiabendazole;thicyofen; thifluzamide; thiophanate-methyl; thiram; tioxymid;tolclofos-methyl; tolylfluanid; triadimefon; triadimenol; triazbutil;triazoxide; tricyclamide; tricyclazole; tridemorph; trifloxystrobin;triflumizole; triforine; triticonazole; uniconazole; validamycin A;vinclozolin; zineb; ziram; zoxamide;(2S)—N-[2-[4-[[3-(4-chlorophenyl)-2-propynyl]oxy]-3-methoxyphenyl]ethyl]-3-methyl-2-[(methylsulphonyl)amino]-butanamide;1-(1-naphthalenyl)-1H-pyrrole-2,5-dione;2,3,5,6-tetrachloro-4-(methylsulphonyl)-pyridine;2-amino-4-methyl-N-phenyl-5-thiazolecarboxamide;2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide;3,4,5-trichloro-2,6-pyridinedicarbonitrile; actinovate;cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol; methyl1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate;monopotassium carbonate;N-(6-methoxy-3-pyridinyl)cyclopropanecarboxamide;N-butyl-8-(1,1-dimethylethyl)-1-oxaspiro-[4.5]decane-3-amine; sodiumtetrathiocarbonate; and copper salts and preparations, such as Bordeauxmixture; copper hydroxide; copper naphthenate; copper oxychloride;copper sulphate; cufraneb; cuprous oxide; mancopper; oxine-copper.

Bactericides:

bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin,probenazole, streptomycin, tecloftalam, copper sulphate and other copperpreparations.

Insecticides/Acaricides/Nematicides: Acetylcholine Esterase (AChE)Inhibitors

-   1.1 Carbamates,    -   for example alanycarb, aldicarb, aldoxycarb, allyxycarb,        aminocarb, bendiocarb, benfuracarb, bufencarb, butacarb,        butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan,        cloethocarb, dimetilan, ethiofencarb, fenobucarb, fenothiocarb,        formetanate, furathiocarb, isoprocarb, metam-sodium, methiocarb,        methomyl, metolcarb, oxamyl, pirimicarb, promecarb, propoxur,        thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb, triazamate-   1.2 Organophosphates,    -   for example acephate, azamethiphos, azinphos (-methyl, -ethyl),        bromophos-ethyl, brom-fenvinfos (-methyl), butathiofos,        cadusafos, carbophenothion, chlorethoxyfos, chlorfenvinphos,        chlormephos, chlorpyrifos (-methyl/-ethyl), coumaphos,        cyanofenphos, cyanophos, chlorfenvinphos, demeton-5-methyl,        demeton-5-methyl sulphone, dialifos, diazinon, dichlofenthion,        dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos,        dioxabenzofos, disulfoton, EPN, ethion, ethoprophos, etrimfos,        famphur, fenamiphos, fenitrothion, fensulfothion, fenthion,        flupyrazofos, fonofos, formothion, fosmethilan, fosthiazate,        heptenophos, iodofenphos, iprobenfos, isazofos, isofenphos,        isopropyl O-salicylate, isoxathion, malathion, mecarbam,        methacrifos, methamidophos, methidathion, mevinphos,        monocrotophos, naled, omethoate, oxydemeton-methyl, parathion        (-methyl/-ethyl), phenthoate, phorate, phosalone, phosmet,        phosphamidon, phosphocarb, phoxim, pirimiphos (-methyl/-ethyl),        profenofos, propaphos, propetamphos, prothiofos, prothoate,        pyraclofos, pyridaphenthion, pyridathion, quinalphos, sebufos,        sulfotep, sulprofos, tebupirimfos, temephos, terbufos,        tetrachlorvinphos, thiometon, triazophos, triclorfon,        vamidothion

Sodium Channel Modulators/Voltage-Gated Sodium Channel Blockers

-   2.1 Pyrethroids,    -   for example acrinathrin, allethrin (d-cis-trans, d-trans),        beta-cyfluthrin, bifenthrin, bioallethrin, bioallethrin-S        cyclopentyl isomer, bioethanomethrin, biopermethrin,        bioresmethrin, chlovaporthrin, cis-cypermethrin, cis-resmethrin,        cis-permethrin, clocythrin, cycloprothrin, cyfluthrin,        cyhalothrin, cypermethrin (alpha-, beta-, theta-, zeta-),        cyphenothrin, deltamethrin, empenthrin (1R isomer),        esfenvalerate, etofenprox, fenfluthrin, fenpropathrin,        fenpyrithrin, fenvalerate, flubrocythrinate, flucythrinate,        flufenprox, flumethrin, fluvalinate, fubfenprox,        gamma-cyhalothrin, imiprothrin, kadethrin, lambda-cyhalothrin,        metofluthrin, permethrin (cis-, trans-), phenothrin (1R        trans-isomer), prallethrin, profluthrin, protrifenbute,        pyresmethrin, resmethrin, RU 15525, silafluofen,        tau-fluvalinate, tefluthrin, terallethrin, tetramethrin (1R        isomer), tralomethrin, transfluthrin, ZXI 8901, pyrethrins        (pyrethrum)    -   DDT-   2.2 Oxadiazines,    -   for example indoxacarb-   2.3 Semicarbazones    -   for example metaflumizone (BAS 3201)

Acetylcholine Receptor Agonists/Antagonists

-   3.1 Chloronicotinyls,    -   for example acetamiprid, clothianidin, dinotefuran,        imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam-   3.2 Nicotine, bensultap, cartap

Acetylcholine Receptor Modulators

-   4.1 Spinosyns,    -   for example spinosad

GABA-Gated Chloride Channel Antagonists

-   5.1 Organochlorines,    -   for example camphechlor, chlordane, endosulfan, gamma-HCH, HCH,        heptachlor, lindane, methoxychlor-   5.2 Fiproles,    -   for example acetoprole, ethiprole, fipronil, pyrafluprole,        pyripole, vaniliprole

Chloride Channel Activators

-   6.1 Mectins,    -   for example avermectin, emamectin, emamectin benzoate,        ivermectin, milbemycin

Juvenile Hormone Mimetics,

-   -   for example diofenolan, epofenonane, fenoxycarb, hydroprene,        kinoprene, methoprene, pyriproxifen, triprene

Ecdyson Agonists/Disruptors

-   8.1 Diacylhydrazines,    -   for example chromafenozide, halofenozide, methoxyfenozide,        tebufenozide

Chitin Biosynthesis Inhibitors

-   9.1 Benzoylureas,    -   for example bistrifluoron, chlofluazuron, diflubenzuron,        fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron,        novaluron, noviflumuron, penfluoron, teflubenzuron, triflumuron-   9.2 Buprofezin-   9.3 Cyromazine

Oxidative Phosphorylation Inhibitors, ATP Disruptors

-   10.1 Diafenthiuron-   10.2 Organotins,    -   for example azocyclotin, cyhexatin, fenbutatin oxide

Oxidative Phosphorylation Decouplers Acting by Interrupting the H-ProtonGradient

-   11.1 Pyrroles,    -   for example chlorfenapyr-   11.2 Dinitrophenols,    -   for example binapacyrl, dinobuton, dinocap, DNOC

Electron Transport Inhibitors

-   12.1 Site-I electron transport inhibitors    -   from the group of    -   METIs,    -   for example fenazaquin, fenpyroximate, pyrimidifen, pyridaben,        tebufenpyrad, tolfenpyrad and also    -   hydramethylnon    -   dicofol-   12.2 Site-II electron transport inhibitors    -   rotenone, cyflumetofen, cyenopyrafen-   12.3 Site-III electron transport inhibitors    -   acequinocyl, fluacrypyrim

Microbial Disruptors of the Insect Gut Membrane

-   -   Bacillus thuringiensis strains

Fatty Acid Biosynthesis Inhibitors

-   14.1 Tetronic acids,    -   for example spirodiclofen, spiromesifen-   14.2 Tetramic acids,    -   for example spirotetramat,        cis-3-(2,5-dimethylphenyl)-4-hydroxy-8-methoxy-1-aza-spiro[4.5]dec-3-en-2-one

Carboxamides,

-   -   for example flonicamid

Octopaminergic Agonists,

-   -   for example amitraz

Inhibitors of Magnesium-Stimulated ATPase,

-   -   propargite

Ryanodin Receptor Effectors

-   -   18.1 benzodicarboxamides,        -   for example flubendiamide    -   18.2 anthranilamides, for example rynaxapyr, HGW86

Nereistoxin Analogues,

-   -   for example thiocyclam hydrogen oxalate, thiosultap-sodium

Biologicals, Hormones or Pheromones

-   -   azadirachtin, Bacillus spec., Beauveria spec., codlemone,        Metarrhizium spec., Paecilomyces spec., thuringiensin,        Verticillium spec.        Active Compounds with Unknown or Unspecific Mechanisms of Action

-   21.1 Fumigants,    -   for example aluminium phosphide, methyl bromide, sulphuryl        fluoride

-   21.2 Antifeedants,    -   for example cryolite, flonicamid, pymetrozine

-   21.3 Mite growth inhibitors,    -   for example clofentezine, etoxazole, hexythiazox

-   21.4 Amidoflumet, benclothiaz, benzoximate, bifenazate,    bromopropylate, buprofezin, chino-methionat, chlordimeform,    chlorobenzilate, chloropicrin, clothiazoben, cycloprene,    cyflumetofen, dicyclanil, fenoxacrim, fentrifanil, flubenzimine,    flufenerim, flutenzin, gossyplure, hydramethylnone, japonilure,    metoxadiazone, petroleum, piperonyl butoxide, potassium oleate,    pyridalyl, sulfluramid, tetradifon, tetrasul, triarathene, verbutin

A mixture with other known active compounds, such as herbicides,fertilizers, growth regulators, safeners, semiochemicals, or else withagents which improve plant properties is also possible.

When used as insecticides in their commercially available formulationsand in the use forms prepared from these formulations, the activecompounds/active compound combinations according to the invention canfurthermore be present in the form of a mixture with synergists.Synergists are compounds by which the activity of the active compoundsis increased without it being necessary for the synergist added to beactive itself.

When used as insecticides in their commercially available formulationsand in the use forms prepared from these formulations, the activecompounds/active compound combinations according to the invention canfurthermore be present in the form of mixtures with inhibitors whichreduce the degradation of the active compound after application in thesurroundings of the plant, on the surface of parts of plants or in planttissues.

The active compound content of the use forms prepared from thecommercially available formulations can vary within wide ranges. Theactive compound concentration of the use forms can be from 0.00000001 upto 95% by weight of active compound and is preferably between 0.00001and 1% by weight.

Application is in a customary manner adapted to suit the use forms.

As already mentioned above, it is possible to treat all plants and theirparts in accordance with the invention. In a preferred embodiment, wildplant species and plant cultivars which have been obtained bytraditional biological breeding methods, such as hybridization orprotoplast fusion, and the parts of these varieties and cultivars aretreated. In a further preferred embodiment, transgenic plants and plantcultivars which have been obtained by recombinant methods, ifappropriate in combination with conventional methods (geneticallymodified organisms), and their parts are treated. The terms “parts” or“parts of plants” or “plant parts” have been explained above.

Plants which are treated particularly preferably in accordance with theinvention are those of the plant cultivars which are in each casecommercially available or in use. Plant cultivars are understood asmeaning plants with new traits which have been bred either byconventional breeding, by mutagenesis or by recombinant DNA techniques.They may take the form of cultivars, biotypes and genotypes.

Depending on the plant species or plant cultivars, their location andgrowth conditions (soils, climate, vegetation period, nutrition), thetreatment according to the invention may also result in superadditive(“synergistic”) effects. Thus, for example, reduced application ratesand/or a widened activity spectrum and/or an increase in the activity ofthe substances and compositions which can be used in accordance with theinvention, better plant growth, increased tolerance to high or lowtemperatures, increased tolerance to drought or to salinity in the wateror soil, increased flowering performance, facilitated harvesting,accelerated maturation, higher harvest yields, higher quality and/orhigher nutritional value of the harvested products, better storagecharacteristics and/or processability of the harvested products arepossible which exceed the effects which were actually to be expected.

The preferred transgenic plants or plant cultivars (those obtained byrecombinant methods) to be treated in accordance with the inventioninclude all those plants which, owing to the process of recombinantmodification, were given genetic material which confers particular,advantageous, valuable traits to these plants. Examples of suchproperties are better plant growth, increased tolerance to high or lowtemperatures, increased tolerance to drought or to salinity in the wateror soil, increased flowering performance, facilitated harvesting,accelerated maturation, higher harvest yields, higher quality and/orhigher nutritional value of the harvested products, better storagecharacteristics and/or processability of the harvested products. Furtherexamples of such traits, examples which must be particularly emphasized,are better defense of the plants against animal and microbial pests,such as against insects, mites, phytopathogenic fungi, bacteria and/orviruses and an increased tolerance of the plants to certain herbicidalactive compounds. Examples of transgenic plants which may be mentionedare the important crop plants, such as cereals (wheat, rice), maize,soybeans, potatoes, sugar beet, tomatoes, peas and other vegetablevarieties, cotton, tobacco, oilseed rape and fruit plants (with thefruits apples, pears, citrus fruits and grapes), with particularemphasis on maize, soybeans, potatoes, cotton, tobacco and oilseed rape.Traits which are especially emphasized are the increased defense of theplants against insects, arachnids, nematodes and slugs and snails, owingto toxins being formed in the plants, in particular toxins which aregenerated in the plants by the genetic material of Bacillusthuringiensis (for example by the genes CryIA(a), CryIA(b), CryIA(c),CryIIA, CryIIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryIF and theircombinations) (hereinbelow “Bt plants”). Other traits which areparticularly emphasized are the increased defense of plants againstfungi, bacteria and viruses by systemic acquired resistance (SAR),systemin, phytoalexins, elicitors and resistance genes andcorrespondingly expressed proteins and toxins. Other traits which areespecially emphasized are the increased tolerance of the plants tocertain herbicidal active compounds, for example imidazolinones,sulphonylureas, glyphosate or phosphinotricin (for example “PAT” gene).The genes which confer the desired traits in each case may also bepresent in the transgenic plants in combination with one another.Examples of “Bt plants” which may be mentioned are maize cultivars,cotton cultivars, soybean cultivars and potato cultivars which arecommercially available under the trade names YIELD GARD® (for examplemaize, cotton, soybeans), KnockOut® (for example maize), StarLink® (forexample maize), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf®(potato). Examples of herbicide-tolerant plants which may be mentionedare maize cultivars, cotton cultivars and soybean cultivars which arecommercially available under the trade names Roundup Ready® (toleranceto glyphosate, for example maize, cotton, soybeans), Liberty Link®(tolerance to phosphinotricin, for example oilseed rape), IMI®(tolerance to imidazolinones) and STS® (tolerance to sulphonylureas, forexample maize). Herbicide-resistant plants (plants bred in aconventional manner for herbicide tolerance) which may be mentioned alsoinclude the varieties commercially available under the name Clearfield®(for example maize). Naturally, these statements also apply to plantcultivars having these genetic traits or genetic traits still to bedeveloped, which plant cultivars will be developed and/or marketed inthe future.

The plants listed can be treated particularly advantageously accordingto the invention with the compounds of the general formula I or theactive compound mixtures according to the invention. The preferredranges stated above for the active compounds and mixtures also apply tothe treatment of these plants. Particular emphasis may be given to thetreatment of plants with the compounds or mixtures specificallymentioned in the present text.

The active compounds/active compound combinations according to theinvention are not only active against plant, hygiene and stored-productpests, but also, in the veterinary medicine sector, against animalparasites (ectoparasites and endoparasites), such as ixodid ticks,argasid ticks, scab mites, trombiculid mites, flies (stinging andsucking), parasitic fly larvae, lice, hair lice, bird lice and fleas.These parasites include:

From the order of the Anoplurida, for example, Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.

From the order of the Mallophagida and the sub-orders Amblycerina andIschnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp.,Bovicola spp., Wemeckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp., Felicola spp.

From the order of the Diptera and the sub-orders Nematocerina andBrachycerina, for example, Aedes spp., Anopheles spp., Culex spp.,Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp.,Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanusspp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp.,Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fanniaspp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp.,Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp.,Gasterophilus spp., Hippobosca spp., Lipoptena spp. and Melophagus spp.

From the order of the Siphonapterida, for example, Pulex spp.,Ctenocephalides spp., Xenopyslla spp. and Ceratophyllus spp.

From the order of the Heteropterida, for example, Cimex spp., Triatomaspp., Rhodnius spp. and Panstrongylus spp.

From the order of the Blattarida, for example, Blatta orientalis,Periplaneta americana, Blattela germanica and Supella spp.

From the sub-class of the Acari (Acarina) and the orders of the Meta-and Mesostigmata, for example, Argas spp., Ornithodorus spp., Otobiusspp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp.,Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp.,Raillietia spp., Pneumonyssus spp., Stemostoma spp. and Varroa spp.

From the order of the Actinedida (Prostigmata) and Acaridida(Astigmata), for example, Acarapis spp., Cheyletiella spp.,Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp.,Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp.,Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp.,Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp. and Laminosioptes spp.

The active compounds/active compound combinations of the formula (I)according to the invention are also suitable for controlling arthropodswhich attack agricultural livestock, such as, for example, cattle,sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits,chickens, turkeys, ducks, geese, honeybees, other domestic animals, suchas, for example, dogs, cats, cage birds, aquarium fish, and so-calledexperimental animals, such as, for example, hamsters, guinea-pigs, ratsand mice. By combating these arthropods, it is intended to reduce deathsand decreased performances (in meat, milk, wool, hides, eggs, honey andthe like), so that more economical and simpler animal keeping is madepossible by using the active compounds according to the invention.

In the veterinary sector and in the case of animal keeping, the activecompounds/active compound combinations according to the invention areused in a known manner by enteral administration, for example in theform of tablets, capsules, drinks, drenches, granules, pastes, boli, thefeed-through method, suppositories, by parenteral administration, suchas, for example, by means of injections (intramuscular, subcutaneous,intravenous, intraperitoneal and the like), implants, by nasalapplication, by dermal administration, for example in the form ofdipping or bathing, spraying, pouring-on and spotting-on, washing,dusting, and with the aid of shaped articles which comprise activecompound, such as collars, ear tags, tail marks, limb bands, halters,marking devices and the like.

When administered to livestock, poultry, domestic animals and the like,the active compounds of the formula (I) can be used as formulations (forexample powders, emulsions, flowables) which comprise the activecompounds in an amount of 1 to 80% by weight, either directly or afterdilution by a factor of 100 to 10 000, or they may be used in the formof a chemical bath.

Furthermore, it has been found that the compounds/active compoundcombinations according to the invention have a potent insecticidalaction against insects which destroy industrial materials.

The following insects may be mentioned by way of example and as beingpreferred, but without any limitation:

Beetles, such as Hylotrupes bajulus, Chlorophorus pilosis, Anobiumpunctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobiumpertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctusafricanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens,Trogoxylon aequale, Minthes rugicollis, Xyleborus spec. Tryptodendronspec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus,Sinoxylon spec. Dinoderus minutus;Dermapterans, such as Sirex juvencus, Urocerus gigas, Urocerus gigastaignus, Urocerus augur;Termites, such as Kalotermes flavicollis, Cryptotermes brevis,Heterotermes indicola, Reticulitermes flavipes, Reticulitermessantonensis, Reticulitermes lucifugus, Mastotermes darwiniensis,Zootermopsis nevadensis, Coptotermes formosanus;Bristletails, such as Lepisma saccharina.

Industrial materials are to be understood as meaning, in the presentcontext, non-live materials, such as, preferably, synthetic materials,glues, sizes, paper and board, leather, wood and timber products, andpaint.

The materials to be very particularly preferably protected againstattack by insects are wood and timber products.

Wood and timber products which can be protected by the compositionaccording to the invention or mixtures comprising such a composition areto be understood as meaning, for example:

construction timber, wooden beams, railway sleepers, bridge components,jetties, wooden vehicles, boxes, pallets, containers, telephone poles,wood cladding, windows and doors made of wood, plywood, particle board,joiner's articles, or wood products which, quite generally, are used inthe construction of houses or in joinery.

The active compounds can be used as such, in the form of concentrates orgenerally customary formulations, such as powders, granules, solutions,suspensions, emulsions or pastes.

The formulations mentioned can be prepared in a manner known per se, forexample by mixing the active compounds with at least one solvent ordiluent, emulsifier, dispersant and/or binder or fixative, waterrepellent, if appropriate desiccants and UV stabilizers and, ifappropriate, colorants and pigments and other processing auxiliaries.

The insecticidal compositions or concentrates used for the protection ofwood and wooden materials comprise the active compound according to theinvention in a concentration of 0.0001 to 95% by weight, in particular0.001 to 60% by weight.

The amount of the compositions or concentrates employed depends on thespecies and the occurrence of the insects and on the medium. The optimumrate of application can be determined upon use in each case by a testseries. However, in general, it suffices to employ 0.0001 to 20% byweight, preferably 0.001 to 10% by weight, of the active compound, basedon the material to be protected.

The solvent and/or diluent used is an organochemical solvent or solventmixture and/or an oily or oil-type organochemical solvent or solventmixture of low volatility and/or a polar organochemical solvent orsolvent mixture and/or water and, if appropriate, an emulsifier and/orwetting agent.

Organochemical solvents which are preferably employed are oily oroil-type solvents having an evaporation number of above 35 and a flashpoint of above 30° C., preferably above 45° C. Substances which are usedas such oily and oil-type solvents which have low volatility and areinsoluble in water are suitable mineral oils or their aromaticfractions, or mineral-oil-containing solvent mixtures, preferably whitespirit, petroleum and/or alkylbenzene.

Substances which are advantageously used are mineral oils with a boilingrange of 170 to 220° C., white spirit with a boiling range of 170 to220° C., spindle oil with a boiling range of 250 to 350° C., petroleumor aromatics of boiling range 160 to 280° C., essence of turpentine andthe like.

In a preferred embodiment, liquid aliphatic hydrocarbons with a boilingrange of 180 to 210° C. or high-boiling mixtures of aromatic andaliphatic hydrocarbons with a boiling range of 180 to 220° C. and/orspindle oil and/or monochloronaphthalene, preferablyα-monochloronaphthalene, are used.

The organic oily or oil-type solvents of low volatility having anevaporation number of above 35 and a flash point of above 30° C.,preferably above 45° C., can be partially replaced by organochemicalsolvents of high or medium volatility, with the proviso that the solventmixture also has an evaporation number of above 35 and a flash point ofabove 30° C., preferably above 45° C., and that theinsecticide/fungicide mixture is soluble or emulsifiable in this solventmixture.

In a preferred embodiment, part of the organochemical solvent or solventmixture or an aliphatic polar organochemical solvent or solvent mixtureis replaced. Substances which are preferably used are aliphaticorganochemical solvents having hydroxyl and/or ester and/or ethergroups, such as, for example, glycol ethers, esters and the like.

The organochemical binders used within the scope of the presentinvention are the synthetic resins and/or binding drying oils which areknown per se and can be diluted with water and/or are soluble ordispersible or emulsifiable in the organochemical solvents employed, inparticular binders composed of, or comprising, an acrylate resin, avinyl resin, for example polyvinyl acetate, polyester resin,polycondensation or polyaddition resin, polyurethane resin, alkyd resinor modified alkyd resin, phenol resin, hydrocarbon resin, such asindene/cumarone resin, silicone resin, drying vegetable and/or dryingoils and/or physically drying binders based on a natural and/orsynthetic resin.

The synthetic resin used as the binder can be employed in the form of anemulsion, dispersion or solution. Up to 10% by weight of bitumen orbituminous substances can also be used as binders. In addition,colorants, pigments, water repellents, odour-masking substances andinhibitors or anticorrosives known per se and the like can be employed.

The composition or the concentrate preferably comprises, in accordancewith the invention, at least one alkyd resin or modified alkyd resinand/or a drying vegetable oil as the organochemical binder. Preferablyused according to the invention are alkyd resins with an oil content ofover 45% by weight, preferably 50 to 68% by weight.

All or some of the abovementioned binder can be replaced by a fixative(mixture) or a plasticizer (mixture). These additives are intended toprevent volatilization of the active compounds and crystallization orprecipitation. They preferably replace 0.01 to 30% of the binder (basedon 100% of binder employed).

The plasticizers are from the chemical classes of the phthalic esters,such as dibutyl phthalate, dioctyl phthalate or benzyl butyl phthalate,the phosphoric esters, such as tributyl phosphate, the adipic esters,such as di(2-ethylhexyl) adipate, the stearates, such as butyl stearateor amyl stearate, the oleates, such as butyl oleate, the glycerol ethersor relatively high molecular weight glycol ethers, glycerol esters andp-toluenesulphonic esters.

Fixatives are chemically based on polyvinyl alkyl ethers, such as, forexample, polyvinyl methyl ether, or ketones, such as benzophenone orethylenebenzophenone.

Particularly suitable as a solvent or diluent is also water, ifappropriate as a mixture with one or more of the abovementionedorganochemical solvents or diluents, emulsifiers and dispersants.

Particularly effective protection of wood is achieved by large-scaleindustrial impregnation processes, for example vacuum, double-vacuum orpressure processes.

If appropriate, the ready-to-use compositions can additionally compriseother insecticides and, if appropriate, additionally one or morefungicides.

Suitable additional components which may be admixed are, preferably, theinsecticides and fungicides mentioned in WO 94/29 268. The compoundsmentioned in that document are expressly part of the presentapplication.

Very particularly preferred components which may be admixed areinsecticides, such as chlorpyriphos, phoxim, silafluofin, alphamethrin,cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25,flufenoxuron, hexaflumuron, transfluthrin, thiacloprid, methoxyphenoxid,triflumuron, chlothianidin, spinosad, tefluthrin,

and fungicides, such as epoxyconazole, hexaconazole, azaconazole,propiconazole, tebuconazole, cyproconazole, metconazole, imazalil,dichlorfluanid, tolylfluanid, 3-iodo-2-propynyl butylcarbamate,N-octyl-isothiazolin-3-one and 4,5-dichloro-N-octylisothiazolin-3-one.

The compounds according to the invention can at the same time beemployed for protecting objects which come into contact with saltwateror brackish water, in particular hulls, screens, nets, buildings,moorings and signalling systems, against fouling.

Fouling by sessile Oligochaeta, such as Serpulidae, and by shells andspecies from the Ledamorpha group (goose barnacles), such as variousLepas and Scalpellum species, or by species from the Balanomorpha group(acorn barnacles), such as Balanus or Pollicipes species, increases thefrictional drag of ships and, as a consequence, leads to a markedincrease in operation costs owing to higher energy consumption andadditionally frequent residence in the dry dock.

Apart from fouling by algae, for example Ectocarpus sp. and Ceramiumsp., fouling in particular by sessile Entomostraka groups, which comeunder the generic term Cirripedia (cirriped crustaceans), is ofparticular importance.

Surprisingly, it has now been found that the compounds according to theinvention, alone or in combination with other active compounds, have anoutstanding antifouling action.

Using the compounds according to the invention, alone or in combinationwith other active compounds, allows the use of heavy metals such as, forexample, in bis(trialkyltin) sulphides, tri-n-butyltin laurate,tri-n-butyltin chloride, copper(I) oxide, triethyltin chloride,tri-n-butyl(2-phenyl-4-chlorophenoxy)tin, tributyltin oxide, molybdenumdisulphide, antimony oxide, polymeric butyl titanate,phenyl(bispyridine)bismuth chloride, tri-n-butyltin fluoride, manganeseethylenebisthio-carbamate, zinc dimethyldithiocarbamate, zincethylenebisthiocarbamate, zinc salts and copper salts of 2-pyridinethiol1-oxide, bisdimethyldithiocarbamoylzinc ethylenebisthiocarbamate, zincoxide, copper(I) ethylenebisdithiocarbamate, copper thiocyanate, coppernaphthenate and tributyltin halides to be dispensed with, or theconcentration of these compounds to be substantially reduced.

If appropriate, the ready-to-use antifouling paints can additionallycomprise other active compounds, preferably algicides, fungicides,herbicides, molluscicides, or other antifouling active compounds.

Preferably suitable components in combination with the antifoulingcompositions according to the invention are:

algicides such as2-tert-butylamino-4-cyclopropylamino-6-methylthio-1,3,5-triazine,dichlorophen, diuron, endothal, fentin acetate, isoproturon,methabenzthiazuron, oxyfluorfen, quinoclamine and terbutryn;fungicides such asbenzo[b]thiophenecarboxylic acid cyclohexylamide S,S-dioxide,dichlofluanid, fluorfolpet, 3-iodo-2-propynyl butylcarbamate,tolylfluanid and azoles such asazaconazole, cyproconazole, epoxyconazole, hexaconazole, metconazole,propiconazole and tebuconazole;molluscicides such asfentin acetate, metaldehyde, methiocarb, niclosamid, thiodicarb andtrimethacarb, Fe chelates;or conventional antifouling active compounds such as4,5-dichloro-2-octyl-4-isothiazolin-3-one, diiodomethylparatrylsulphone, 2-(N,N-dimethyl-thiocarbamoylthio)-5-nitrothiazyl, potassium,copper, sodium and zinc salts of 2-pyridinethiol 1-oxide,pyridinetriphenylborane, tetrabutyldistannoxane,2,3,5,6-tetrachloro-4-(methylsulphonyl)-pyridine,2,4,5,6-tetrachloroisophthalonitrile, tetramethylthiuram disulphide and2,4,6-trichlorophenylmaleimide.

The antifouling compositions used comprise the active compound accordingto the invention of the compounds according to the invention in aconcentration of 0.001 to 50% by weight, in particular 0.01 to 20% byweight.

Moreover, the antifouling compositions according to the inventioncomprise the customary components such as, for example, those describedin Ungerer, Chem. Ind. 1985, 37, 730-732 and Williams, AntifoulingMarine Coatings, Noyes, Park Ridge, 1973.

Besides the algicidal, fungicidal, molluscicidal active compounds andinsecticidal active compounds according to the invention, antifoulingpaints comprise, in particular, binders.

Examples of recognized binders are polyvinyl chloride in a solventsystem, chlorinated rubber in a solvent system, acrylic resins in asolvent system, in particular in an aqueous system, vinyl chloride/vinylacetate copolymer systems in the form of aqueous dispersions or in theform of organic solvent systems, butadiene/styrene/acrylonitrilerubbers, drying oils such as linseed oil, resin esters or modifiedhardened resins in combination with tar or bitumens, asphalt and epoxycompounds, small amounts of chlorine rubber, chlorinated polypropyleneand vinyl resins.

If appropriate, paints also comprise inorganic pigments, organicpigments or colorants which are preferably insoluble in saltwater.Paints may furthermore comprise materials such as rosin to allowcontrolled release of the active compounds. Furthermore, the paints maycomprise plasticizers, modifiers which affect the rheological propertiesand other conventional constituents. The compounds according to theinvention or the abovementioned mixtures may also be incorporated intoself-polishing antifouling systems.

The active compounds are also suitable for controlling animal pests, inparticular insects, arachnids and mites, which are found in enclosedspaces such as, for example, dwellings, factory halls, offices, vehiclecabins and the like. They can be employed in domestic insecticideproducts for controlling these pests alone or in combination with otheractive compounds and auxiliaries. They are active against sensitive andresistant species and against all development stages. These pestsinclude:

From the order of the Scorpionidea, for example, Buthus occitanus.

From the order of the Acarina, for example, Argas persicus, Argasreflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus,Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi,Neutrombicula autumnalis, Dermatophagoides pteronissimus,Dermatophagoides forinae.

From the order of the Araneae, for example, Aviculariidae, Araneidae.

From the order of the Opiliones, for example, Pseudoscorpiones chelifer,Pseudoscorpiones cheiridium, Opiliones phalangium.

From the order of the Isopoda, for example, Oniscus asellus, Porcellioscaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus,Polydesmus spp.

From the order of the Chilopoda, for example, Geophilus spp.

From the order of the Zygentoma, for example, Ctenolepisma spp., Lepismasaccharina, Lepismodes inquilinus.

From the order of the Blattaria, for example, Blatta orientalies,Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchloraspp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana,Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa.

From the order of the Saltatoria, for example, Acheta domesticus.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Kalotermes spp.,Reticulitermes spp.

From the order of the Psocoptera, for example, Lepinatus spp.,Liposcelis spp.

From the order of the Coleptera, for example, Anthrenus spp., Attagenusspp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp.,Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae,Sitophilus zeamais, Stegobium paniceum.

From the order of the Diptera, for example, Aedes aegypti, Aedesalbopictus, Aedes taeniorhynchus, Anopheles spp., Calliphoraerythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culexpipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Muscadomestica, Phlebotomus spp., Sarcophaga camaria, Simulium spp., Stomoxyscalcitrans, Tipula paludosa.

From the order of the Lepidoptera, for example, Achroia grisella,Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tineapellionella, Tineola bisselliella.

From the order of the Siphonaptera, for example, Ctenocephalides canis,Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsyllacheopis.

From the order of the Hymenoptera, for example, Camponotus herculeanus,Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis,Paravespula spp., Tetramorium caespitum.

From the order of the Anoplura, for example, Pediculus humanus capitis,Pediculus humanus corporis, Phthirus pubis.

From the order of the Heteroptera, for example, Cimex hemipterus, Cimexlectularius, Rhodinus prolixus, Triatoma infestans.

They are used in the household insecticides sector alone or incombination with other suitable active compounds such as phosphoricesters, carbamates, pyrethroids, neonicotinoids, growth regulators oractive compounds from other known classes of insecticides.

They are used in aerosols, pressure-free spray products, for examplepump and atomizer sprays, automatic fogging systems, foggers, foams,gels, evaporator products with evaporator tablets made of cellulose orpolymer, liquid evaporators, gel and membrane evaporators,propeller-driven evaporators, energy-free, or passive, evaporationsystems, moth papers, moth bags and moth gels, as granules or dusts, inbaits for spreading or in bait stations.

The active compounds/active compound combinations according to theinvention can also be used as defoliants, desiccants, haulm killers and,in particular, as weed killers. Weeds in the broadest sense areunderstood as meaning all plants which grow at locations where they areundesired. Whether the substances according to the invention act asnonselective or selective herbicides depends essentially on theapplication rate.

The active compounds/active compound combinations according to theinvention can be used, for example, in the following plants:

Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia,Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus,Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium,Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus,Ipomoea, Kochia, Lamium, Lepidium, Lindemia, Matricaria, Mentha,Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum,Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola,Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola,Xanthium.Dicotyledonous crops of the genera: Arachis, Beta, Brassica, Cucumis,Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca,Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis,Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina,Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis,Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera,Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum,Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria,Sorghum.Monocotyledonous crops of the genera: Allium, Ananas, Asparagus, Avena,Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale,Triticum, Zea.

However, the use of the active compounds/active compound combinationsaccording to the invention is in no way restricted to these genera, butalso extends in the same manner to other plants.

Depending on the concentration, the active compounds/active compoundcombinations according to the invention are suitable for thenonselective weed control on, for example, industrial terrains andrailway tracks and on paths and locations with and without trees.Likewise the active compounds according to the invention can be employedfor controlling weeds in perennial crops, for example forests,ornamental tree plantings, orchards, vineyards, citrus groves, nutorchards, banana plantations, coffee plantations, tea plantations,rubber plantations, oil palm plantations, cocoa plantations, soft fruitplantations and hop fields, on lawns, turf and pastureland, and for theselective control of weeds in annual crops.

The compounds of the formula (I)/active compound combinations accordingto the invention have strong herbicidal activity and a broad activityspectrum when used on the soil and on aerial plant parts. To a certainextent, they are also suitable for the selective control ofmonocotyledonous and dicotyledonous weeds in monocotyledonous anddicotyledonous crops, both pre- and post-emergence.

At certain concentrations or application rates, the activecompounds/active compound combinations according to the invention canalso be employed for controlling animal pests and fungal or bacterialplant diseases. If appropriate, they can also be used as intermediatesor precursors for the synthesis of other active compounds.

The active compounds/active compound combinations can be converted intothe customary formulations, such as solutions, emulsions, wettablepowders, suspensions, powders, dusting agents, pastes, soluble powders,granules, suspoemulsion concentrates, natural and synthetic materialsimpregnated with active compound, and microencapsulations in polymericsubstances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents and/orsolid carriers, optionally with the use of surfactants, that isemulsifiers and/or dispersants and/or foam formers.

If the extender used is water, it is also possible to use, for example,organic solvents as auxiliary solvents. Suitable liquid solvents areessentially: aromatics, such as xylene, toluene or alkylnaphthalenes,chlorinated aromatics and chlorinated aliphatic hydrocarbons, such aschlorobenzenes, chloroethylenes or methylene chloride, aliphatichydrocarbons, such as cyclohexane or paraffins, for example petroleumfractions, mineral and vegetable oils, alcohols, such as butanol orglycol, and also their ethers and esters, ketones, such as acetone,methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, stronglypolar solvents, such as dimethylformamide and dimethyl sulphoxide, andalso water.

Suitable solid carriers are: for example ammonium salts and groundnatural minerals, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as highly disperse silica, alumina and silicates;suitable solid carriers for granules are: for example crushed andfractionated natural rocks such as calcite, marble, pumice, sepioliteand dolomite, and also synthetic granules of inorganic and organicmeals, and granules of organic material such as sawdust, coconut shells,maize cobs and tobacco stalks; suitable emulsifiers and/or foam formersare: for example nonionic and anionic emulsifiers, such aspolyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers,for example alkylaryl polyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates and protein hydrolysates; suitabledispersants are: for example lignosulphite waste liquors andmethylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, and also naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Other possible additivesare mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian blue, and organic colorants,such as alizarin colorants, azo colorants and metal phthalocyaninecolorants, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 percent by weightof active compound, preferably between 0.5 and 90%.

The active compounds/active compound combinations according to theinvention, as such or in their formulations, can also be used for weedcontrol purposes as a mixture with known herbicides and/or withsubstances which improve crop plant tolerance (“safeners”), ready mixesor tank mixes being possible. Mixtures with herbicide products whichcontain one or more known herbicides and a safener are hence alsopossible.

Herbicides which are suitable for the mixtures are known herbicides, forexample

acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim(-sodium), ametryne, amicarbazone, amidochlor, amidosulfuron,aminopyralid, anilofos, asulam, atrazine, azafenidin, azimsulfuron,beflubutamid, benazolin (-ethyl), benfuresate, bensulfuron (-methyl),bentazone, bencarbazone, benzfendizone, benzobicyclon, benzofenap,benzoylprop (-ethyl), bialaphos, bifenox, bispyribac (-sodium),bromobutide, bromofenoxim, bromoxynil, butachlor, butafenacil (-allyl),butroxydim, butylate, cafenstrole, caloxydim, carbetamide, carfentrazone(-ethyl), chlomethoxyfen, chloramben, chloridazon, chlorimuron (-ethyl),chlomitrofen, chlorsulfuron, chlortoluron, cinidon (-ethyl),cinmethylin, cinosulfuron, clefoxydim, clethodim, clodinafop(-propargyl), clomazone, clomeprop, clopyralid, clopyrasulfuron(-methyl), cloransulam (-methyl), cumyluron, cyanazine, cybutryne,cycloate, cyclosulfamuron, cycloxydim, cyhalofop (-butyl), 2,4-D,2,4-DB, desmedipham, diallate, dicamba, dichlorprop (—P), diclofop(-methyl), diclosulam, diethatyl (-ethyl), difenzoquat, diflufenican,diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn,dimethenamid, dimexyflam, dinitramine, diphenamid, diquat, dithiopyr,diuron, dymron, epropodan, EPTC, esprocarb, ethalfluralin,ethametsulfuron (-methyl), ethofumesate, ethoxyfen, ethoxysulfuron,etobenzanid, fenoxaprop (—P-ethyl), fentrazamide, flamprop (-isopropyl,-isopropyl-L, -methyl), flazasulfuron, florasulam, fluazifop (—P-butyl),fluazolate, flucarbazone (-sodium), flufenacet, flumetsulam, flumiclorac(-pentyl), flumioxazin, flumipropyn, flumetsulam, fluometuron,fluorochloridone, fluoroglycofen (-ethyl), flupoxam, flupropacil,flurpyrsulfuron (-methyl, -sodium), flurenol (-butyl), fluridone,fluoroxypyr (-butoxypropyl, -meptyl), flurprimidol, flurtamone,fluthiacet (-methyl), fluthiamide, fomesafen, foramsulfuron, glufosinate(-ammonium), glyphosate (-isopropylammonium), halosafen, haloxyfop(-ethoxyethyl, —P-methyl), hexazinone, HOK-201, imazamethabenz(-methyl), imazamethapyr, imazamox, imazapic, imazapyr, imazaquin,imazethapyr, imazosulfuron, iodosulfuron (-methyl, -sodium), ioxynil,isopropalin, isoproturon, isouron, isoxaben, isoxachlortole,isoxaflutole, isoxapyrifop, lactofen, lenacil, linuron, MCPA, mecoprop,mefenacet, mesosulfuron, mesotrione, metamifop, metamitron, metazachlor,methabenzthiazuron, metobenzuron, metobromuron, (alpha-) metolachlor,metosulam, metoxuron, metribuzin, metsulfuron (-methyl), molinate,monolinuron, naproanilide, napropamide, neburon, nicosulfuron,norflurazon, orbencarb, orthosulfamuron, oryzalin, oxadiargyl,oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat,pelargonic acid, pendimethalin, pendralin, penoxsulam, pentoxazone,phenmedipham, picolinafen, pinoxaden, piperophos, pretilachlor,primisulfuron (-methyl), profluazol, prometryn, propachlor, propanil,propaquizafop, propisochlor, propoxycarbazone (-sodium), propyzamide,prosulfocarb, prosulfuron, pyraflufen (-ethyl), pyrasulfotole,pyrazogyl, pyrazolate, pyrazosulfuron (-ethyl), pyrazoxyfen,pyribenzoxim, pyributicarb, pyridate, pyridatol, pyriftalid, pyriminobac(-methyl), pyrimisulfan, pyrithiobac (-sodium), pyroxsulam,pyroxasulfone, quinchlorac, quinmerac, quinoclamine, quizalofop(—P-ethyl, —P-tefuryl), rimsulfuron, sethoxydim, simazine, simetryn,sulcotrione, sulfentrazone, sulfometuron (-methyl), sulfosate,sulfosulfuron, tebutam, tebuthiuron, tembotrione, tepraloxydim,terbuthylazine, terbutryn, thenylchlor, thiafluamide, thiazopyr,thidiazimin, thiencarbazone-methyl thifensulfuron (-methyl),thiobencarb, tiocarbazil, topramezone, tralkoxydim, triallate,triasulfuron, tribenuron (-methyl), triclopyr, tridiphane, trifluralin,trifloxysulfuron, triflusulfuron (-methyl), tritosulfuron and

A mixture with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellents, plant nutrientsand soil conditioners, is also possible.

The active compounds/active compound combinations can be used as such,in the form of their formulations or the use forms prepared therefrom byfurther dilution, such as ready-to-use solutions, suspensions,emulsions, powders, pastes and granules. They are applied in thecustomary manner, for example by pouring, spraying, atomizing,spreading.

The active compounds/active compound combinations according to theinvention can be applied both before and after plant emergence. They canalso be incorporated into the soil prior to sowing.

The application rate of active compound can vary within a substantialrange. Essentially, it depends on the nature of the desired effect. Ingeneral, the application rates are between 1 g and 10 kg of activecompound per hectare of soil area, preferably between 5 g and 5 kg perha.

The substances/active compound combinations according to the inventionhave potent microbicidal activity and can be employed for controllingunwanted microorganisms, such as fungi and bacteria, in crop protectionand in the protection of materials.

Fungicides can be employed in crop protection for controllingPlasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes,Ascomycetes, Basidiomycetes and Deuteromycetes.

Bactericides can be employed in crop protection for controllingPseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceaeand Streptomycetaceae.

Some pathogens causing fungal and bacterial diseases which come underthe generic names listed above may be mentioned as examples, but not byway of limitation:

Xanthomonas species, such as, for example, Xanthomonas campestris pv.oryzae;Pseudomonas species, such as, for example, Pseudomonas syringae pv.lachrymans;Erwinia species, such as, for example, Erwinia amylovora;Pythium species, such as, for example, Pythium ultimum;Phytophthora species, such as, for example, Phytophthora infestans;Pseudoperonospora species, such as, for example, Pseudoperonosporahumuli or Pseudoperonospora cubensis;Plasmopara species, such as, for example, Plasmopara viticola;Bremia species, such as, for example, Bremia lactucae;Peronospora species, such as, for example, Peronospora pisi or P.brassicae;Erysiphe species, such as, for example, Erysiphe graminis;Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;Podosphaera species, such as, for example, Podosphaera leucotricha;Venturia species, such as, for example, Venturia inaequalis;Pyrenophora species, such as, for example, Pyrenophora teres or P.graminea(conidia form: Drechslera, syn: Helminthosporium);Cochliobolus species, such as, for example, Cochliobolus sativus(conidia form: Drechslera, syn: Helminthosporium);Uromyces species, such as, for example, Uromyces appendiculatus;Puccinia species, such as, for example, Puccinia recondita;Sclerotinia species, such as, for example, Sclerotinia sclerotiorum;Tilletia species, such as, for example, Tilletia caries;Ustilago species, such as, for example, Ustilago nuda or Ustilagoavenae;Pellicularia species, such as, for example, Pellicularia sasakii;Pyricularia species, such as, for example, Pyricularia oryzae;Fusarium species, such as, for example, Fusarium culmorum;Botrytis species, such as, for example, Botrytis cinerea;Septoria species, such as, for example, Septoria nodorum;Leptosphaeria species, such as, for example, Leptosphaeria nodorum;Cercospora species, such as, for example, Cercospora canescens;Alternaria species, such as, for example, Alternaria brassicae; andPseudocercosporella species, such as, for example, Pseudocercosporellaherpotrichoides.

The active compounds/active compound combinations according to theinvention also have very good fortifying action in plants. Accordingly,they can be used for mobilizing the defenses of the plant against attackby unwanted microorganisms.

In the present context, plant-fortifying (resistance-inducing)substances are to be understood as meaning those substances which arecapable of stimulating the defense system of plants such that, when thetreated plants are subsequently inoculated with unwanted microorganisms,they show substantial resistance against these microorganisms.

In the present case, unwanted microorganisms are to be understood asmeaning phytopathogenic fungi, bacteria and viruses. Accordingly, thesubstances according to the invention can be used to protect plants fora certain period after the treatment against attack by the pathogensmentioned. The period for which protection is provided generally extendsover 1 to 10 days, preferably 1 to 7 days, after the treatment of theplants with the active compounds.

The fact that the active compounds/active compound combinations are welltolerated by plants at the concentrations required for controlling plantdiseases permits the treatment of above-ground parts of plants, ofpropagation stock and seeds, and of the soil.

The active compounds/active compound combinations according to theinvention are also suitable for increasing the yield of crops. Inaddition, they show reduced toxicity and are well tolerated by plants.

At certain concentrations and application rates, the activecompounds/active compound combinations according to the invention can,if appropriate, also be used as herbicides, for influencing plant growthand for controlling animal pests. If appropriate, they can also be usedas intermediates and precursors for the synthesis of further activecompounds.

In the protection of materials, the substances according to theinvention can be employed for protecting industrial materials againstinfection with, and destruction by, unwanted microorganisms. Industrialmaterials in the present context are understood as meaning non-livingmaterials which have been prepared for use in industry. For example,industrial materials which are intended to be protected by activecompounds according to the invention from microbial change ordestruction can be adhesives, sizes, paper and board, textiles, leather,wood, paints and plastic articles, cooling lubricants and othermaterials which can be infected with, or destroyed by, microorganisms.Parts of production plants, for example cooling-water circuits, whichmay be impaired by the proliferation of microorganisms may also bementioned within the scope of the materials to be protected. Industrialmaterials which may be mentioned within the scope of the presentinvention are preferably adhesives, sizes, paper and board, leather,wood, paints, cooling lubricants and heat-transfer liquids, particularlypreferably wood.

Microorganisms capable of degrading or changing the industrial materialswhich may be mentioned are, for example, bacteria, fungi, yeasts, algaeand slime organisms. The active compounds according to the inventionpreferably act against fungi, in particular moulds, wood-discolouringand wood-destroying fungi (Basidiomycetes), and against slime organismsand algae.

Microorganisms of the following genera may be mentioned as examples:

Alternaria, such as Alternaria tenuis,Aspergillus, such as Aspergillus niger,Chaetomium, such as Chaetomium globosum,Coniophora, such as Coniophora puetana,Lentinus, such as Lentinus tigrinus,Penicillium, such as Penicillium glaucum,Polyporus, such as Polyporus versicolor,Aureobasidium, such as Aureobasidium pullulans,Sclerophoma, such as Sclerophoma pityophila,Trichoderma, such as Trichoderma viride,Escherichia, such as Escherichia coli,Pseudomonas, such as Pseudomonas aeruginosa, andStaphylococcus, such as Staphylococcus aureus.

Depending on their particular physical and/or chemical properties, theactive compounds/active compound combinations can be converted into thecustomary formulations, such as solutions, emulsions, suspensions,powders, foams, pastes, granules, aerosols and microencapsulations inpolymeric substances and in coating compositions for seeds, and ULV cooland warm fogging formulations.

These formulations are produced in a known manner, for example by mixingthe active compounds/active compound combinations with extenders, thatis liquid solvents, liquefied gases under pressure, and/or solidcarriers, optionally with the use of surfactants, that is emulsifiersand/or dispersants, and/or foam formers. If the extender used is water,it is also possible to employ, for example, organic solvents asauxiliary solvents. Essentially, suitable liquid solvents are: aromaticssuch as xylene, toluene or alkylnaphthalenes, chlorinated aromatics orchlorinated aliphatic hydrocarbons such as chlorobenzenes,chloroethylenes or methylene chloride, aliphatic hydrocarbons such ascyclohexane or paraffins, for example petroleum fractions, alcohols suchas butanol or glycol and their ethers and esters, ketones such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents such as dimethylformamide and dimethylsulphoxide, or else water. Liquefied gaseous extenders or carriers areto be understood as meaning liquids which are gaseous at standardtemperature and under atmospheric pressure, for example aerosolpropellants such as halogenated hydrocarbons, or else butane, propane,nitrogen and carbon dioxide. Suitable solid carriers are: for exampleground natural minerals such as kaolins, clays, talc, chalk, quartz,aftapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals such as highly disperse silica, alumina and silicates. Suitablesolid carriers for granules are: for example crushed and fractionatednatural rocks such as calcite, marble, pumice, sepiolite and dolomite,or else synthetic granules of inorganic and organic meals, and granulesof organic material such as sawdust, coconut shells, maize cobs andtobacco stalks. Suitable emulsifiers and/or foam formers are: forexample nonionic and anionic emulsifiers, such as polyoxyethylene fattyacid esters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates,or else protein hydrolysates. Suitable dispersants are: for examplelignosulphite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, or else naturalphospholipids such as cephalins and lecithins and syntheticphospholipids can be used in the formulations. Other possible additivesare mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian blue, and organic colorants suchas alizarin colorants, azo colorants and metal phthalocyanine colorants,and trace nutrients such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 percent by weightof active compound, preferably between 0.5 and 90%.

The active compounds/active compound combinations according to theinvention can be used as such or in their formulations, also in amixture with known fungicides, bactericides, acaricides, nematicides orinsecticides, to broaden, for example, the activity spectrum or toprevent development of resistance. In many cases, synergistic effectsare obtained, i.e. the activity of the mixture is greater than theactivity of the individual components.

Examples of suitable mixing components are the compounds mentionedabove.

A mixture with other known active compounds, such as herbicides, or withfertilizers and growth regulators, is also possible.

In addition, the compounds of the formula (I)/active compoundcombinations according to the invention also have very good antimycoticactivity. They have a very broad antimycotic activity spectrum inparticular against dermatophytes and yeasts, moulds and diphasic fungi(for example against Candida species, such as Candida albicans, Candidaglabrata), and Epidermophyton floccosum, Aspergillus species, such asAspergillus niger and Aspergillus fumigatus, Trichophyton species, suchas Trichophyton mentagrophytes,

Microsporon species such as Microsporon canis and audouinii. The list ofthese fungi by no means limits the mycotic spectrum covered, but is onlyfor illustration.

The active compounds/active compound combinations can be used as such,in the form of their formulations or the use forms prepared therefrom,such as ready-to-use solutions, suspensions, wettable powders, pastes,soluble powders, dusting agents and granules. Application is carried outin a customary manner, for example by pouring, spraying, atomizing,broadcasting, dusting, foaming, spreading, etc. It is furthermorepossible to apply the active compounds by the ultra-low-volume method,or to inject the active compound preparation or the active compounditself into the soil. It is also possible to treat the seeds of theplants.

When using the active compounds/active compounds combinations accordingto the invention as fungicides, the application rates can be variedwithin a relatively wide range, depending on the kind of application.For the treatment of parts of plants, the active compound applicationrates are generally between 0.1 and 10 000 g/ha, preferably between 10and 1000 g/ha. For seed dressing, the active compound application ratesare generally between 0.001 and 50 g per kilogram of seed, preferablybetween 0.01 and 10 g per kilogram of seed. For the treatment of thesoil, the active compound application rates are generally between 0.1and 10 000 g/ha, preferably between 1 and 5000 g/ha.

The preparation and the use of the active compounds/active compoundcombinations according to the invention are illustrated by the examplesbelow.

EXAMPLES Example I-a-1

2.3 g (20 mmol) of potassium tert-butoxide are introduced under an argonatmosphere in 7 ml of N,N-dimethylacetamide (DMA) and this initialcharge is admixed dropwise at 80° C. with 3.6 g (9 mmol) of the compoundof Example II-1 in 7 ml of DMA and stirred at 80° C. for 1 hour. Afterend of reaction (thin-layer-chromatographic control (TLC control)) thereaction mixture is added to 80 ml of ice-water and at 0 to 10° C. isbrought to a pH of 2 using 1N hydrochloric acid, and the precipitate isfiltered off with suction, washed and dried.

Yield: 3.18 g (94% of theory), m.p. 211° C.

Example I-a-2

0.7 g of3-(4-bromo-2-ethyl-6-methylphenyl)-5-methoxymethyl-5-methylpyrrolidine-2,4-dioneand 0.71 g of 4-chlorophenylboronic acid are introduced in 5 ml ofdimethoxyethane and this initial charge is admixed with 0.01 g oftetrakistriphenylphosphinepalladium and 15 ml of 7.5% strength Na₂CO₃solution and stirred under reflux and under inert gas for 6 h. Themixture is added to water, adjusted to a pH of 1 using 1N HCl, stirredat room temperature for 10 minutes and filtered with suction on a frit.

Yield: 0.5 g (65% of theory), m.p. 206-209° C.

¹H-NMR (300 MHz, d₆-DMSO): δ=1.30 (d, 3H,

2.17 (d, 3H, aryl-CH ₃) ppm.

In analogy to Examples (I-a-1) and (I-a-2) and in accordance with thegeneral preparation details the following compounds are obtained of theformula (I-a)

(I-a)

Ex. No. W X Y Z A B D m.p. ° C. I-a-3 C₂H₅ C₂H₅ 4-Cl-Ph H —CH₂— CH₃ OCH₃217-218 I-a-4 CH₃ C₂H₅ 4-CH₃-Ph H —CH₂— CH₃ OCH₃ *1.28 (d, 3 H,

2.14 (d, 3 H, Ar—CH ₃) I-a-5 CH₃ CH₃ 4-CH₃-Ph H —CH₂— CH₃ OCH₃ 321-323I-a-6 H Cl H 4-Cl-Ph —CH₂— CH₃ OCH₃ 189 I-a-7 CH₃ CH₃ H 4-Cl-Ph —CH₂—CH₃ OCH₃ 200 I-a-8 CH₃ CH₃ H 4-F-Ph —CH₂— CH₃ OCH₃ 182 I-a-9 H CH₃ H4-CH₃-Ph —CH₂— CH₃ OCH₃  66 I-a-10 CH₃ CH₃ H 3,4-Cl₂-Ph —CH₂— CH₃ OCH₃112 I-a-11 H CH₃ H 3-F, 4-Cl-Ph —CH₂— CH₃ OCH₃ decomp. I-a-12 H CH₃ H4-F-Ph —CH₂— CH₃ OCH₃ *1.31 (s, 3 H, CH ₃), 2.20 (s, 3H, Ar—CH ₃), 3.22(s, 3 H, OCH ₃) I-a-13 H CH₃ H 4-C₂H₅-Ph —CH₂— CH₃ OCH₃ 105 I-a-14 H CH₃H 3,4-F₂-Ph —CH₂— CH₃ OCH₃  85 I-a-15 H CH₃ H 4-Cl-Ph — CH₃

226 isomer mixture I-a-16 H Cl H 4-Cl-Ph — CH₃

216 isomer mixture I-a-17 H CH₃ H 4-F-Ph — CH₃

191 isomer mixture I-a-18 CH₃ CH₃ H 4-F-Ph — CH₃

243 isomer mixture I-a-19 CH₃ CH₃ H 4-Cl-Ph — CH₃

245 isomer mixture I-a-20 H Cl H 4-F-Ph —CH₂— CH₃ OCH₃ 201 I-a-21 H CH₃H 4-Cl-Ph —(CH₂)₂— CH₃ OCH₃ 222 I-a-22 CH₃ CH₃ H 4-F-Ph —(CH₂)₂— CH₃OCH₃ 184 I-a-23 H CH₃ H 4-F-Ph —(CH₂)₂— CH₃ OCH₃ 184 I-a-24 CH₃ CH₃ H4-Cl-Ph —(CH₂)₂— CH₃ OCH₃ 186 I-a-25 CH₃ CH₃ H 4-Cl-Ph —CH₂— CH₃

215 I-a-26 H Cl H 4-F-Ph —(CH₂)₂— CH₃ OCH₃ 191 I-a-27 H Cl H 4-Cl-Ph—(CH₂)₂— CH₃ OCH₃ 194 *¹H-NMR (400 MHz, d₆-DMSO): shifts δ in ppm

Example I-b-1

0.154 g (0.4 mmol) of the compound of Ex. I-a-2 are introduced in 8 mlof ethyl acetate and then this initial charge is admixed with 0.07 ml oftriethylamine and 1.5 mg of DMAP and heated to 50° C. Subsequently 2 mlof a solution of 0.05 ml of isobutyryl chloride in ethyl acetate areadded dropwise in 5 portions over the course of 30 min. The mixture isstirred under reflux for 6 h and then stirred at room temperatureovernight. Saturated NaCl solution is added and the organic phase isseparated off. After drying with sodium sulphate it is purified bycolumn chromatography (ethyl acetate/n-heptane 1:4 to 4:1).

Yield: 0.127 g (70% of theory).

*¹H-NMR (400 MHz, CDCl₃): δ=1.00 (dd, 6H, CH(CH ₃)₂), 2.30 (s, 3H, Ar—CH₃), 3.41 (d, 3H, OCH ₃) ppm.

In analogy to Example (I-b-1) and in accordance with the generalpreparation details the following compounds are obtained of the formula(I-b)

(I-b)

Ex. No. W X Y Z A B D R¹ m.p. ° C. I-b-2 C₂H₅ C₂H₅ 4-Cl-Ph H —CH₂— CH₃OCH₃ i-C₃H₇ **1.00 (dd, 6 H, CH(CH ₃)₂), 2.59 (m, 5 H, ArCH ₂,CH(CH₃)₂), 3.41 (s, 3 H, OCH ₃) I-b-3 CH₃ CH₃ 4-CH₃-Ph H —CH₂— CH₃ OCH₃H₃CO—CH₂— *2.28 (d, 6 H, ArCH₃), 3.37 (s, 3 H, OCH ₃), 4.00 (q, 2 H,O—CH ₂) I-b-4 CH₃ CH₃ 4-CH₃-Ph H —CH₂— CH₃ OCH₃ i-C₃H₇ **1.01 (d, 6 H,CH(CH ₃)₂), 2.29 (d, 6 H, ArCH ₃), 3.39 (s, 3 H, OCH ₃) I-b-5 CH₃ C₂H₅4-CH₃-Ph H —CH₂— CH₃ OCH₃ i-C₃H₇ **0.96 (ddd, 6 H, CH(CH ₃)₂), 2.29 (d,3 H, Ar—CH ₃), 3.41 (s, 3 H, O—CH ₃) I-b-6 H CH₃ H 4-F-Ph —CH₂— CH₃ OCH₃i-C₃H₇ 152 I-b-7 H CH₃ H 4-Cl-Ph —CH₂— CH₃ OCH₃

 75 I-b-8 H CH₃ H 4-Cl-Ph — CH₃

i-C₃H₇  91 isomer mixture I-b-9 H CH₃ H 3,4-F₂-Ph —CH₂— CH₃ OCH₃ i-C₃H₇103 I-b-10 H CH₃ H 3-F, 4-Cl-Ph —CH₂— CH₃ OCH₃ i-C₃H₇ 157 I-b-11 H CH₃ H4-CH₃-Ph —CH₂— CH₃ OCH₃ i-C₃H₇  59 I-b-12 H Cl H 4-F-Ph —CH₂— CH₃ OCH₃i-C₃H₇ 166 I-b-13 H CH₃ H 4-Cl-Ph —CH₂— CH₃ OCH₃ i-C₃H₇ ***0.94 (“t”, 6H, CH(CH ₃)₂), 3.31 (s, 3 H, OCH ₃), 3.45 (ABq, 2 H, CH ₂OCH₃) I-b-14CH₃ CH₃ H 4-F-Ph —CH₂— CH₃ OCH₃ i-C₃H₇  76 I-b-15 CH₃ CH₃ H 4-Cl-Ph —CH₃

i-C₃H₇ ***0.90-0.97 (m, 6 H, CH(CH ₃)₂), 2.15-2.20 (4 s, 3 H, Ar—CH ₃),7.21-7.24 (AA′, 2 H, Ar—H) 7.45-7.47 (BB′, 2 H, Ar—H) I-b-16 H CH₃ H4-F-Ph — CH₃

i-C₃H₇ ***2.59 (zm, 1 H, CH(CH₃)₂), 3.94-3.98 (m, 1 H, CHO), 7.57-7.62(m, 2 H, Ar—H) I-b-17 H Cl H 4-Cl-Ph — CH₃

i-C₃H₇ ***1.37, 1.40, 1.45 (3 s, 3 H, CH ₃) 2.66 (zm, 1 H, CH(CH₃)₂),3.95-3.98 (m, 1 H, O—CH) I-b-18 H CH₃ H 4-Cl-Ph —CH₂— CH₃ OCH₃ 4-Cl-Ph***1.42 (s, 3 H, CH ₃) 2.24 (s, 3 H, Ar—CH ₃) 3.51-3.59 (ABq, 2 H, OCH₂) 7.58 (AA'd, 2 H, Ar—H) 7.93 (BB'd, 2 H, Ar—H) I-b-19 H Cl H 4-Cl-Ph—CH₂— CH₃ OCH₃ CH₃ decomp. I-b-20 H Cl H 4-Cl-Ph —CH₂— CH₃ OCH₃ i-C₃H₇167 I-b-21 CH₃ CH₃ H 4-F-Ph — CH₃

i-C₃H₇ ***1.99, 2.02 (2 s, 3 H, Ar—CH ₃) 2.17, 2.19 (2 s, 3 H, Ar—CH ₃),3.94-3.98 (m, 1 H, CHO) I-b-22 H CH₃ H 4-Cl-Ph —(CH₂)₂— CH₃ OCH₃ i-C₃H₇***1.37 (s, 3 H, CH ₃) 2.62 (m, 1 H, CH(CH₃)₂, 3.23 (s, 3 H, OCH ₃)I-b-23 CH₃ CH₃ H 4-Cl-Ph —(CH₂)₂— CH₃ OCH₃ i-C₃H₇ ***0.93-0.96 (8 s, 6H, CH(CH ₃)₂, 1.38, 1.40 (2 s, 3 H, CH ₃) 2.15, 2.19 (2 s, 3 H, Ar—CH ₃)3.19, 3.23 (2 s, 3 H, OCH ₃) *¹H-NMR (300 MHz, CDCl₃): shifts δ in ppm**¹H-NMR (400 MHz, CDCl₃): shifts δ in ppm ***¹H-NMR (400 MHz, d₆-DMSO):shifts δ in ppm

Example I-c-1

0.15 g of the compound of Example I-a-2 and 0.06 ml of triethylamine areintroduced in 8 ml of dichloromethane and this initial charge is stirredat room temperature for 5 minutes, admixed with 0.046 g of ethylchloroformate and stirred at room temperature overnight. After end ofreaction (TLC control), 5 ml of Na₂CO₃ solution are added and themixture is stirred at room temperature for 10 minutes, separated via anextraction cartridge and concentrated on a rotary evaporator.Purification is accomplished by column chromatography using ethylacetate/n-heptane (1:4 to 4:1).

Yield: 0.172 g (97% of theory).

*¹H-NMR (300 MHz, CDCl₃): δ=2.24 (s, 3H, Ar—CH ₃), 3.3 (d, 3H, OCH ₃),3.96 (q, 2H, O—CH ₂—CH₃).

In analogy to Example (I-c-1) and in accordance with the generalpreparation details the following compounds are obtained of the formula(I-c)

(I-c)

Ex. No. W X Y Z A B D M R² m. p. ° C. I-c-2 C₂H₅ C₂H₅ 4-Cl-Ph H —CH₂—CH₃ OCH₃ O C₂H₅ *2.63 (m, 4 H, Ar-CH ₂, 3.38 (s, 3 H, OCH ₃, 4.05 (q, 2H, OCH ₂—CH₃) I-c-3 CH₃ CH₃ 4-CH₃-Ph H —CH₂— CH₃ OCH₃ O C₂H₅ **2.38 (s,3 H, Ar—H), 3.41 (s, 3 H, OCH ₃) I-c-4 CH₃ C₂H₅ 4-CH₃-Ph H —CH₂— CH₃OCH₃ O C₂H₅ **2.59 (m, 2 H, Ar—CH ₃), 3.41 (d, 3 H, OCH ₃) 4.03 (q, 2 H,OCH ₂CH₃) I-c-5 H CH₃ H 4-Cl-Ph —CH₂— CH₃ OCH₃ O C₂H₅ wax I-c-6 H Cl H4-Cl-Ph —CH₂— CH₃ OCH₃ O C₂H₅ 154 I-c-7 CH₃ CH₃ H 4-Cl-Ph —CH₂— CH₃ OCH₃O C₂H₅ wax I-c-8 H CH₃ H 4-F-Ph —CH₂— CH₃ OCH₃ O CH₃ ***1.37 (s, 3 H, CH₃), 2.21 (s, 3 H, ArCH ₃), 3.32 (s, 3 H, OCH ₃) 3.60 (s, 3 H, CO₂ CH ₃),I-c-9 CH₃ CH₃ H 3,4-Cl₂-Ph —CH₂— CH₃ OCH₃ O CH₃  68 I-c-10 H Cl H 4-F-Ph—CH₂— CH₃ OCH₃ O C₂H₅  61 1-c-11 H Cl H 4-F-Ph —CH₂— CH₃ OCH₃ O CH₃ 132I-c-12 H CH₃ H 4-F-Ph — CH₃

O CH₃ **1.37, 1.40, 1.47 (3 s, 3 H, CH ₃), 1.81-1.99 (m, 4 H, (CH ₂)₂)I-c-13 H Cl H 4-Cl-Ph — CH₃

O CH₃ **3.62 (2 s, 3 H, CO₂ CH ₃), 7.63-7.7 (m, 3 H, Ar—H) 3.56, 3.57 (2s, 3 H, CO₂ CH ₃) I-c-14 H CH₃ H 4-CH₃-Ph —CH₂— CH₃ OCH₃ O CH₃ 127I-c-15 H CH₃ H 4-Cl-Ph —CH₂— CH₃ OCH₃ O Ph-CH₂ 164 I-c-16 H CH₃ H4-Cl-Ph —CH₂— CH₃ OCH₃ O CH₃ 146 I-c-17 H CH₃ H 4-Cl-Ph —(CH₂)₂— CH₃OCH₃ O C₂H₅ ***0.94 (t, 3 H, CH₂ CH ₃), 1.96 (t, 2 H, CH ₂CH₂—O) 3.96(q, 2 H, O—CH ₂CH₃) I-c-18 H CH₃ H 4-F-Ph —(CH₂)₂— CH₃ OCH₃ O CH₃***1.41 (s, 3 H, CH ₃), 1.96 (t, 2 H, CH ₂—CH₂—O) 3.22 (s, 3 H, OCH ₃)3.56 (s, 3 H, CO₂ CH ₃) I-c-19 CH₃ CH₃ H 4-F-Ph —(CH₂)₂— CH₃ OCH₃ O CH₃***1.41, 1.43 (2 s, 3 H, CH ₃), 2.14, 2.18 (2 s, 3 H, Ar—CH ₃) 3.43 (m,2 H, O—CH ₂) 3.56 (s, 3 H, CO₂ CH ₃) I-c-20 H CH₃ H 4-Cl-Ph —(CH₂)₂— CH₃OCH₃ O CH₃ ***1.96 (t, 2 H, CH ₂—CH₂—O), 2.23 (s, 3 H, Ar—CH ₃) 3.41 (2m, 2 H, O—CH ₂) 3.56 (s, 3 H, CO₂CH ₃) I-c-21 CH₃ CH₃ H 4-Cl-Ph —(CH₂)₂—CH₃ OCH₃ O CH₃ ***1.41, 1.43 (2 s, 3 H, CH ₃), 2.14, 2.18 (2 s, 3 H,ArCH ₃) 1.97, 2.02 (2 s, 3 H, Ar—CH ₃) 3.56 (s, 3 H, CO₂ CH ₃) *¹H-NMR(300 MHz, CDCl₃): shifts δ in ppm **¹H-NMR (400 MHz, CDCl₃): shifts δ inppm ***¹H-NMR (400 MHz, d₆-DMSO): shifts δ in ppm

Example II-1

Under argon, 3.03 g of methyl 2-amino-2-methoxymethylpropionate×HCl(16.5 mmol) are introduced in 75 ml of anhydrous tetrahydrofuran. At 20°C. this initial charge is admixed dropwise with 4.6 ml (33 mmol) oftriethylamine. It is stirred for 5 minutes and admixed at 20° C. with3.9 g of 3-(4-chlorophenyl)-6-methylphenylacetic acid (15 mmol). After15 minutes 3.45 ml of triethylamine (25 mmol) are added dropwise,followed immediately by 0.93 ml of phosphorus oxychloride (10 mmol); thesolution ought to boil moderately. It is stirred under reflux for 30minutes. After end of reaction (TLC control) purification isaccomplished by column chromatography on silica gel(dichloromethane:ethyl acetate=10:1).

Yield: 3.6 g (60% of theory), m.p. 107° C.

In analogy to Example (II-1) and in accordance with the generalpreparation details the following compounds are obtained of the formula(II)

(II)

Ex. No. W X Y Z A B D R⁸ m. p. ° C. II-2 CH₃ CH₃ H 4-Cl-Ph —CH₂— CH₃OCH₃ CH₃ *1.44 (s, 3 H, CH ₃), 2.14, 2.33 (2 s, each 3 H, Ar—CH ₃), 3.25(s, 3 H, CH₂—O—CH ₃), 3.6 (s, 3 H, CO₂ CH ₃) II-3 H Cl H 4-Cl-Ph —CH₂—CH₃ OCH₃ CH₃ *1.46 (s, 3 H, CH ₃), 3.26 (s, 3 H, CH₂—O—CH ₃), 3.61 (s, 3H, CO₂ CH ₃), 3.69 (s, 2 H, CH ₂CO) II-4 H CH₃ H 4-Cl-Ph — CH₃

CH₃ 113 isomer mixture II-5 H CH₃ H 3,4-F₂-Ph —CH₂— CH₃ OCH₃ CH₃ 111II-6 H CH₃ H 4-CH₃-Ph —CH₂— CH₃ OCH₃ CH₃ 133 II-7 CH₃ CH₃ H 3,4-Cl₂-Ph—CH₂— CH₃ OCH₃ CH₃ **1.39 (s, 3 H, CH ₃), 2.11, 2.28 (s, 6 H, Ar—CH ₃),3.27 (s, 3 H, OCH ₃), 3.55 (s, 3 H, CO₂ CH ₃) II-8 CH₃ CH₃ H 4-F-Ph—CH₂— CH₃ OCH₃ CH₃ **2.09, 2.27 (2 s, 6 H, Ar—CH ₃), 3.26 (s, 3 H, OCH₃), 7.18-7.28 (m, 4 H, 4-F-Ar—H) II-9 H CH₃ H 3-F, —CH₂— CH₃ OCH₃ CH₃125 4-Cl-Ph II-10 H CH₃ H 4-F-Ph —CH₂— CH₃ OCH₃ CH₃ 114 II-11 H Cl H4-C₂H₅-Ph —CH₂— CH₃ OCH₃ CH₃ 97 II-12 CH₃ CH₃ H 3-F, —CH₂— CH₃ OCH₃ CH₃**1.39 (s, 3 H, CH ₃), 4-Cl-Ph 3.55 (s, 3 H, CO₂CH₃), 7.59 (“t”, 1,Ar—H) II-13 H CH₃ H 4-F-Ph — CH₃

CH₃ ***1.44, 1.47 (2 s, 3 H, CH ₃), 2.32 (2 s, 3 H, Ar—CH ₃), 3.93-3.98(m, 1 H, O—CH) II-14 CH₃ CH₃ H 4-F-Ph — CH₃

CH₃ ***1.45-1.47 (4 s, 3 H, CH ₃), 2.14, 2.15 (2 s, 3 H, Ar—CH ₃), 2.33,2.34 (3 s, 3 H, Ar—CH ₃), II-15 CH₃ CH₃ H 4-Cl-Ph — CH₃

CH₃ ***1.44, 1.45 (2 s, 3 H, CH ₃), II-16 H Cl H 4-Cl-Ph — CH₃

CH₃ ***1.45-4.48 (2 s, 3 H, CH ₃), 7.44-7.49 (m, 4 H, Ar—H), 7.58-7.63(m, 3 H, Ar—H), II-17 H Cl H 4-F-Ph —CH₂— CH₃ OCH₃ CH₃ 130 II-18 CH₃ CH₃H 4-Cl-Ph —(CH₂)₂— CH₃ OCH₃ CH₃ **1.40 (s, 3 H, CH ₃), 2.11, 2.29 (2 s,6 H, Ar—CH ₃), 3.34 (t, 2 H, O—CH ₂), 3.54 (s, 3 H, CO₂CH ₃) II-19 H CH₃H 4-Cl-Ph —(CH₂)₂— CH₃ OCH₃ CH₃ **2.28 (s, 3 H, CH ₃), 3.29-3.34 (m, 2H, CH ₂), 3.53 (s, 5 H, CH ₂CO, CO₂CH ₃) II-20 CH₃ CH₃ H 4-F-Ph —(CH₂)₂—CH₃ OCH₃ CH₃ **2.10, 2.28 (2 s, 6 H, Ar—CH ₃), 3.34 (t, 2 H, O—CH ₂),3.59 (s, 2 H, COCH ₂) 7.19-7.28 (m, 4 H, F—Ar—H) II-21 H CH₃ H 4-F-Ph—(CH₂)₂— CH₃ OCH₃ CH₃ **1.35 (s, 3 H, CH ₃), 2.28 (s, 3 H, Ar—CH ₃),3.32 (2 m, 2 H, OCH ₂) 7.62-7.65 (m, 2 H, Ar—H) II-22 CH₃ CH₃ H 4-Cl-Ph—CH₂— CH₃

CH₃ **1.44, 1.47 (2 s, 3 H, CH ₃), 2.15, 2.16 (2 s, 3 H, Ar—CH ₃), 2.33,2.34 (2 s, 3 H, Ar—CH ₃) 3.60, 3.61 (2 s, 3 H, CO₂ CH ₃) II-23 H Cl H4-F-Ph —(CH₂)₂— CH₃ OCH₃ CH₃ **1.49 (s, 3 H, CH ₃), 3.10 (s, 3 H, OCH₃), 7.19 (2 m, 2 H, Ar—H) II-24 H Cl H 4-Cl-Ph —(CH₂)₂— CH₃ OCH₃ CH₃**1.49 (s, 3 H, CH ₃), 3.10 (s, 3 H, CH ₃), 3.60 (s, 3 H, CO—CH ₃) 3.67(s, 2 H, CO—CH ₂) *¹H-NMR (300 MHz, CDCl₃): shifts δ in ppm **¹H-NMR(400 MHz, d₆-DMSO): shifts δ in ppm ***¹H-NMR (400 Mhz, CD₃—CN): shiftsδ in ppm

Example XIII-1

Under argon, 189.3 g of the compound of Example XVI-1 are introduced in4.4 l of methanol at 0° C. to 5° C. and this initial charge is admixedslowly dropwise with 230 ml of thionyl chloride. It is stirred at 0° C.for 30 min then at 40° C. for approximately 10 h and is left at roomtemperature overnight. It is cooled to 5° C., the precipitate isfiltered off with suction and the solvent is removed on a rotaryevaporator.

Yield: 197.4 g (96% of theory).

¹H-NMR (400 MHz, d₆-DMSO): δ=1.45 (s, 3H, CH ₃), 3.31 (s, 1H, OCH ₃),3.69 (s, 2H, O—CH ₂), 3.76 (s, 3H, COOCH ₃) ppm.

In analogy to Example XIII-1 the new amino acid esters of the formula(XIII-2) to (XIII-3) are obtained in the form of their salts

¹H-NMR (400 MHz, d₆-DMSO): δ=1.43, 1.5 (2s, 3H, CH ₃), 3.75 (s, 3H, CO₂CH ₃), 4.12 (m, 1H, OCH) ppm and

¹H-NMR (400 MHz, d₆-DMSO): δ=1.52, 1.55 (2s, 3H, CH ₃), 3.71, 3.75 (2s,3H, CO₂ CH ₃), 3.85, 4.03 (m, 1H, OCH) ppm.

Example XVI-1

Under argon, 176.5 g of 5-methoxymethyl-5-methylhydantoin are suspendedin 1700 ml of 30% strength KOH and the suspension is stirred underreflux overnight.

Concentrate to approximately 25% of the volume on a rotary evaporator;acidify at 0-10° C. using concentrated HCl, concentrate on a rotaryevaporator, and dry. The white powder is reacted further directly forthe preparation of Example XIII-1.

In analogy to Example XVI-1 the new amino acids of the formula (XVI-2)to (XVI-3) are obtained

5-Methoxymethyl-5-methylhydantoin (XX-1)

Under argon inert gas, ammonium carbonate (134.5 g) and sodium cyanide(16.17 g) are introduced in 560 ml of water. Beginning at roomtemperature, the methoxyacetone (26.4 g) is added dropwise and thereaction mixture is stirred at 55° C. to 60° C. over four hours and thenstirred at 0° C. to 5° C. for two hours.

The solid is filtered off with suction and dried.

Yield: 21.55 g (45% of theory).

In analogy to Example (XX-1) the new hydantoins (XX-2) to (XX-3) areobtained

¹H-NMR (400 MHz, d₆-DMSO): δ=1.25, 1.40 (2s, 3H, CH ₃), 3.73 (m, 2H, OCH₂), 3.97 (m, 1H, CHO) ppm and

¹H-NMR (400 MHz, d₆-DMSO): δ=1.20, 1.22 (2s, 3H, CH ₃), 3.50-3.86 (m,3H, O—CH ₂, O—CH) ppm.

USE EXAMPLES Example No. 1 Myzus Test (MYZUPE Spray Treatment)

Solvent: 78 parts by weight of acetone 1.5 parts by weight ofdimethylformamide Emulsifier: 0.5 part by weight of alkylaryl polyglycolether

A suitable preparation of active compound is prepared by mixing 1 partby weight of active compound with the stated amounts of solvent andemulsifier and diluting the concentrate with emulsifier-containing waterto the desired concentration.

Leaf discs of Chinese cabbage (Brassica pekinensis) infested by allstages of the green peach aphid (Myzus persicae) are sprayed with apreparation of active compound at the desired concentration.

After the desired time the effect in % is determined. 100% means thatall of the aphids have been killed; 0% means that no aphids have beenkilled.

In this test the following compounds, for example, of the PreparationExamples, applied at a rate of 500 g/ha, show an activity of ≧80%:I-a-1, I-a-6, I-a-8, I-a-9, I-a-10, I-a-11, I-a-12, I-a-14, I-a-15,I-a-16, I-a-17, I-a-18, I-a-19, I-a-20, I-a-21, I-a-22, I-a-23, I-a-24,I-a-25, I-a-26, I-a-27, I-b-6, I-b-7, I-b-8, I-b-9, I-b-10, I-b-12,I-b-13, I-b-14, I-b-15, I-b-16, I-b-17, I-b-18, I-b-22, I-b-23, I-c-5,I-c-6, I-c-7, I-c-8, I-c-9, I-c-10, I-c-11, I-c-12, I-c-13, I-c-17,I-c-18, I-c-19, I-c-20, I-c-21.

Example No. 2 Phaedon Test (PHAECO Spray Treatment)

Solvent: 78 parts by weight of acetone 1.5 parts by weight ofdimethylformamide Emulsifier: 0.5 part by weight of alkylaryl polyglycolether

A suitable preparation of active compound is prepared by mixing 1 partby weight of active compound with the stated amounts of solvent andemulsifier and diluting the concentrate with emulsifier-containing waterto the desired concentration.

Leaf discs of Chinese cabbage (Brassica pekinensis) are sprayed with apreparation of active compound at the desired concentration and afterthey have dried are populated with larvae of the mustard beetle (Phaedoncochleariae).

After the desired time the effect in % is determined. 100% means thatall of the beetle larvae have been killed; 0% means that no beetlelarvae have been killed.

In this test the following compounds, for example, of the PreparationExamples, applied at a rate of 500 g/ha, show an activity of ≧80%:I-a-1, I-a-2, I-a-6, I-a-7, I-a-8, I-a-9, I-a-10, I-a-11, I-a-12,I-a-13, I-a-14, I-a-15, I-a-20, I-a-21, I-a-22, I-a-23, I-a-26, I-a-27,I-b-7, I-b-8, I-b-9, I-b-12, I-b-13, I-b-14, I-b-18, I-b-23, I-c-5,I-c-6, I-c-7, I-c-8, I-c-9, I-c-10, I-c-11, I-c-12, I-c-13.

Example No. 3 Tetranychus Test, OP-Resistant (TETRUR Spray Treatment)

Solvent: 7 parts by weight of dimethylformamide Emulsifier: 2 parts byweight of alkylaryl polyglycol ether

A suitable preparation of active compound is prepared by mixing 1 partby weight of active compound with the stated amounts of solvent andemulsifier and diluting the concentrate with emulsifier-containing waterto the desired concentration.

Bean plants (Phaseolus vulgaris) heavily infested by all stages of thegreenhouse red spider mite (Tetranychus urticae) are immersed in apreparation of active compound at the desired concentration.

After the desired time the effect in % is determined. 100% means thatall of the spider mites have been killed; 0% means that no spider miteshave been killed.

In this test the following compounds, for example, of the PreparationExamples, applied at a rate of 100 g/ha, show an activity of ≧80%:I-a-1, I-a-2, I-a-7, I-a-14, I-a-15, I-a-16, I-a-18, I-a-19, I-a-21,I-a-22, I-a-23, I-a-24, I-a-25, I-a-27, I-b-6, I-b-7, I-b-8, I-b-9,I-b-10, I-b-16, I-b-17, I-b-18, I-b-22, I-b-23, I-c-1, I-c-5, I-c-6,I-c-8, I-c-9, I-c-11, I-c-12, I-c-13, I-c-17, I-c-18, I-c-19, I-c-20,I-c-21.

Example No. 4 Spodoptera frugiperda Test (SPODFR Spray Treatment)

Solvent: 78 parts by weight of acetone 1.5 parts by weight ofdimethylformamide Emulsifier: 0.5 part by weight of alkylaryl polyglycolether

A suitable preparation of active compound is prepared by mixing 1 partby weight of active compound with the stated amounts of solvent andemulsifier and diluting the concentrate with emulsifier-containing waterto the desired concentration.

Leaf discs of maize (Zea mays) are sprayed with a preparation of activecompound at the desired concentration and after they have dried arepopulated with caterpillars of the army worm (Spodoptera frugiperda).

After the desired time the effect in % is determined. 100% means thatall of the caterpillars have been killed; 0% means that no caterpillarshave been killed.

In this test the following compounds, for example, of the PreparationExamples, applied at a rate of 500 g/ha, show an activity of ≧80%:I-a-1, I-a-6, I-a-7, I-a-8, I-a-9, I-a-10, I-a-11, I-a-12, I-a-14,I-a-15, I-a-16, I-a-17, I-a-18, I-a-19, I-a-20, I-a-21, I-a-26, I-a-27,I-b-6, I-b-7, I-b-8, I-b-9, I-b-10, I-b-12, I-b-13, I-b-14, I-b-15,I-b-16, I-b-17, I-b-18, I-b-22, I-b-23, I-c-5, I-c-6, I-c-7, I-c-10,I-c-1, I-c-12, I-c-13, I-c-17, I-c-20, I-c-21.

Example No. 5 Meloidogyne Test (MELGIN Spray Treatment)

Solvent: 80 parts by weight of acetone

A suitable preparation of active compound is prepared by mixing 1 partby weight of active compound with the stated amount of solvent anddiluting the concentrate with water to the desired concentration.

Containers are filled with sand, a solution of active compound,Meloidogyne incognita egg/larvae suspension and lettuce seeds. Thelettuce seeds germinate and the plants develop. On the roots, gallsdevelop.

After the desired time, the nematicidal effect is determined in % fromthe formation of galls. 100% means that no galls were found; 0% meansthat the number of galls on the treated plants corresponds to that ofthe untreated control.

In this test the following compounds, for example, of the PreparationExamples show an activity of ≧80% when applied at a rate of 20 ppm:I-a-8, I-a-11, I-a-22, I-a-23.

Example No. 6 Lucilia cuprina Test (LUCICU)

Solvent: dimethyl sulphoxide

A suitable preparation of active compound is prepared by mixing 1 partby weight of active compound with the stated amount of water anddiluting the concentrate with water to the desired concentration.

Containers with horse meat which has been treated with the preparationof active compound at the desired concentration are populated withLucilia cuprina larvae.

After the desired time the destruction in % is determined. 100% meansthat all of the larvae have been killed; 0% means that no larvae havebeen killed.

In this test the following compounds, for example, of the PreparationExamples exhibit an activity of ≧80% when applied at a rate of 100 ppm:I-a-1, I-a-6, I-a-7, I-c-5, I-c-6, I-c-7.

Example No. 7 Boophilus microplus Test (BOOPMI Injection)

Solvent: dimethyl sulphoxide

A suitable preparation of active compound is prepared by mixing 1 partby weight of active compound with the stated amount of solvent anddiluting the concentrate with solvent to the desired concentration.

The solution of active compound is injected into the abdomen (Boophilusmicroplus) and the animals are transferred into dishes and stored in aclimatized room.

After the desired time the effect in % is determined. In this case 100%means that none of the ticks has laid fertile eggs.

In this test the following compounds, for example, of the PreparationExamples show an activity of ≧80% when applied at a rate of 20μg/animal: I-a-1, I-a-6, I-a-7, I-c-5, I-c-6, I-c-7.

Example No. 8 1. Pre-Emergence Herbicidal Effect

Seeds of monocotyledonous and dicotyledonous weed plants and crop plantsare placed in sandy loam soil in wood fibre pots and are covered withearth. The test compounds, formulated in the form of wettable powders(WP), are then applied, in the form of an aqueous suspension, at a waterapplication rate of 600 l/ha (converted) and with addition of 0.2%wetting agent, in different dosages, to the surface of the coveringearth.

After the treatment the pots are placed in a greenhouse and held undergood growth conditions for the test plants. The visual assessment of theemergence damage on the trial plants is carried out after a trial periodof 3 weeks by comparison with untreated controls (herbicidal effect inpercent: 100% effect=plants have died, 0% effect=like control plants).

In addition to the aforementioned compounds, the following compounds at320 g/ha a.i. show a pre-emergence effect of ≧80% against Loliummultiflorum and Setaria viridis: I-a-2, I-a-3, I-a-4, I-a-5, I-a-6,I-a-16, I-a-19, I-b-1, I-b-2, I-b-3, I-b-5, I-b-6, I-b-7, I-b-8, I-b-22,I-c-2, I-c-3, I-c-4, I-c-5, I-c-6, I-c-7, I-c-21.

2. Post-Emergence Herbicidal Effect

Seeds of monocotyledonous and dicotyledonous weed plants and crop plantsare placed in sandy loam soil in wood fibre pots and are covered withearth and cultivated in a greenhouse under good growth conditions. 2-3weeks after sowing, the trial plants are treated at the one-leaf stage.The test compounds, formulated as wettable powders (WP), are sprayedonto the green parts of the plants, at various dosages, with a waterapplication rate of 600 l/ha (converted) and with addition of 0.2%wetting agent. After the trial plants have stood in the greenhouse forabout 3 weeks under optimum growth conditions, the effect of theproducts is rated visually in comparison to untreated controls(herbicidal effect in percent: 100% effect=plants have died, 0%effect=like control plants).

As well as the aforementioned compounds, the following compounds show apost-emergence effect of ≧80% at 320 g/ha a.i. against Echinocloacrus-galli, Lolium multiflorum and Setaria viridis: I-a-1, I-a-2, I-a-3,I-a-4, I-a-5, I-b-1, I-b-2, I-b-3, I-c-2.

As well as the aforementioned compounds, the following compounds show apost-emergence effect of ≧80% at 80 g/ha against Echinocloa crus-galliand Setaria viridis: I-a-6, I-a-7, I-a-19, I-a-24, I-b-7, I-b-22, I-c-5,I-c-20.

Example No. 9 1. Post-Emergence Herbicidal Effect

Seeds of monocotyledonous and dicotyledonous weed plants and crop plantsare placed in sandy loam soil in wood fibre pots or in plastic pots andare covered with earth and cultivated in a greenhouse and also, duringthe vegetation period, outdoors, outside of the greenhouse, under goodgrowth conditions. 2 to 3 weeks after sowing, the trial plants aretreated at the one- to three-leaf stage. The test compounds, formulatedas wettable powders (WP) or liquids (EC), are sprayed onto the plantsand the soil surface in various dosages, with a water application rateof 300 l/ha (converted) and with addition of wetting agent (0.2% to0.3%). 3 to 4 weeks after the trial plants have been treated, the effectof the products is rated visually in comparison to untreated controls(herbicidal effect in percent: 100% effect=plants have died, 0%effect=like control plants).

Use of Safeners:

If the testing is also to look at whether safeners can improve thetolerance of the crop plants for test substances, the following optionsare used for the application of the safener:

-   -   seeds of the crop plants are dressed with the safener substance        prior to sowing (the amount of safener is stated as a        percentage, based on the seed weight)    -   crop plants are sprayed with the safener, with a defined        application rate per hectare, prior to application of the test        substances (typically 1 day before the test substances are        applied)    -   the safener is applied together with the test substance in the        form of a tank mix (the amount of safener is reported in g/ha or        as a proportion relative to the herbicide).

2. Pre-Emergence Herbicidal Effect

Seeds of monocotyledonous and dicotyledonous weed plants and crop plantsare placed in sandy loam soil in wood fibre pots or in plastic pots andare covered with earth. The test compounds, formulated as wettablepowders (WP) or liquids (EC), are sprayed onto the soil surface invarious dosages, with a water application rate of 300 l/ha (converted).The pots are then placed in a greenhouse under good growth conditions,and also, during the vegetation period, are placed outdoors, outside ofthe greenhouse, so that the plants are able to germinate and develop. 3to 4 weeks after the trial plants have been treated, the effect of theproducts is rated visually in comparison to untreated controls(herbicidal effect in percent: 100% effect=plants have died, 0%effect=like control plants).

Use of Safeners:

If the testing is also to look at whether safeners can improve thetolerance of the crop plants for test substances, the following optionsare used for the application of the safener:

-   -   seeds of the crop plants are dressed with the safener substance        prior to sowing (the amount of safener is stated as a        percentage, based on the seed weight)    -   pots containing the crop plants are sprayed with the safener,        with a defined application rate per hectare, prior to        application of the test substances    -   the safener is applied together with the test substance in the        form of a tank mix (the amount of safener is reported in g/ha or        as a proportion relative to the herbicide).

By comparing the effect of test substances on crop plants which havebeen treated with safener and without safener it is possible to assessthe effect of the safener substance.

Greenhouse Container Trials with Cereals Mefenpyr 1 Day Prior toHerbicide Application Post-Emergence

10 days after application Application rate Spring barley Spring wheat ga.i./ha observed (%) observed (%) Ex. I-b-5 100 65 15 50 50 10 Ex.I-b-5 + 100 + 100 50 8 mefenpyr  50 + 100 20 5

28 days after application Application rate Spring barley g a.i./haobserved (%) Ex. I-b-5 100 30 25 10 Ex. I-b-5 + 100 + 100 15 mefenpyr 50 + 100 5

Greenhouse Container Trials with Maize Ex. II-e-5 1 Day Prior toHerbicide Application Pre-Emergence

28 days after application Application rate Maize - Arsenal g a.i./haobserved (%) Ex. I-c-1 50 55 Ex. I-c-1 + 100 + 100 20 Ex. II-e-5

28 days after application Application rate Maize - Arsenal g a.i./haobserved (%) Ex. I-b-2 50 50 25 40 Ex. I-b-2 + 50 + 200 25 Ex. II-e-525 + 200 20

Example 10 Boosting of Penetration into the Plant by Ammonium Salts orPhosphonium Salts, and Synergistic Boosting of Penetration into thePlant by Ammonium/Phosphonium Salts in Combination with PenetrationPromoters

This test measures the penetration of active compounds throughenzymatically isolated cuticles of apple leaves.

The leaves used were cut in the fully developed state from apple treesof the Golden Delicious variety. The cuticles were isolated as follows:

-   -   first of all, leaf discs labelled on the underside with dye and        formed by punching were filled by means of vacuum infiltration        with a pectinase solution (0.2% to 2% strength) buffered to a pH        of between 3 and 4,    -   the sodium azide was then added and    -   the leaf discs thus treated were left to stand until the        original leaf structure broke down and the non-cellular cuticle        underwent detachment.

After that, only those cuticles from the top leaf sides that were freefrom stomata and hairs were used. They were washed a number of times inalternation with water and with a buffer solution, pH 7. The cleancuticles obtained were, finally, applied to Teflon plaques, smoothedwith a gentle jet of air, and dried.

In the next step the cuticular membranes obtained in this way wereplaced in stainless steel diffusion cells (transport chambers) for thepurpose of membrane transport investigations. For these investigationsthe cuticles were placed centrally using tweezers on the edges of thediffusion cells, which were coated with silicone grease, and sealed witha ring, which was likewise greased. The arrangement had been chosen sothat the morphological outer side of the cuticles was directed outwards,in other words facing the air, while the original inner side was facingthe inside of the diffusion cell.

The diffusion cells were filled with a 30% strength ethyleneglycol/water solution. Penetration was determined by applying 10 μl ofthe spray liquor of the composition below to the outer side of each ofthe cuticles. The spray liquor is prepared using local mains water ofmedium hardness.

After the spray liquors had been applied, the water was evaporated andthen the chambers were inverted and placed in thermostated troughs, inwhich the temperature and humidity over the cuticles was adjustable bymeans of a gentle stream of air onto the cuticles, with the spraycoating (20° C., 60% rh). At regular intervals, samples were taken usingan autosampler, and the amount of active compound was determined usingHPLC.

The results of the experiment are apparent from the table below. Thenumbers stated represent average values from 5 to 6 measurements. It canclearly be seen that ammonium sulphate, even on its own, significantlyimproves the penetration, and that together with RME there is asuperadditive (synergistic) effect.

Penetration after 24 h/% EC + AS EC + RME EC + RME (1 g/l) + EC + RME (1g/l) + Active compound EC (1 g/l) (1 g/l) AS (1 g/l) ADHP (1 g/l)Example I-a-7 1.7 7.1 7.1 29.6 22.3 0.2 g/l in water/acetone 6:4 RME =Rapeseed oil methyl ester (formulated for use as 500 EW, concentrationfigure in g active compound/l) AS = ammonium sulphate ADHP = ammoniumdihydrogen phosphate EC = emulsifiable concentrate

Example 11 Activity Boost Through Ammonium/Phosphonium Salts inCombination with Penetration Promoters

Myzus persicae Test

Solvent: 7 parts by weight of dimethylformamide Emulsifier: 2 parts byweight of alkylaryl polyglycol ether

A suitable preparation of active compound is prepared by mixing 1 partby weight of active compound with the stated amounts of solvent andemulsifier and diluting the concentrate with water to the desiredconcentration. For application with ammonium salts or phosphonium saltsand penetration promoters (rapeseed oil methyl ester 500 EW) these arein each case added in a concentration of 1000 ppm to the spray liquor.

Bell pepper plants (Capsicum annuum) heavily infested by the green peachaphid (Myzus persicae) are sprayed to runoff with the preparation ofactive compound at the desired concentration.

After the desired time the destruction in % is determined. 100% meansthat all of the animals have been killed; 0% means that no animals havebeen killed.

TABLE Active Concen- +AS +RME com- tration Destruction +AS +RME 1000 ppmpound (ppm) (%) after 6 d 1000 ppm 1000 pm each I-a-1 20 0 65 98 99 4 00 35 75 I-a-12 100 85 98 99 99 20 10 0 45 99

Example 12

Aphis gossypii Test

Solvent: 7 parts by weight of dimethylformamide Emulsifier: 2 parts byweight of alkylaryl polyglycol ether

A suitable preparation of active compound is prepared by mixing 1 partby weight of active compound with the stated amounts of solvent andemulsifier and diluting the concentrate with emulsifier-containing waterto the desired concentration. For application with ammonium salts orphosphonium salts and penetration promoters (rapeseed oil methyl ester500 EW) these are in each case added in a concentration of 1000 ppm a.i.to the spray liquor.

Cotton plants (Gossypium hirsutum) heavily infested by the cotton aphid(Aphis gossypii) are sprayed to runoff with the preparation of activecompound at the desired concentration.

After the desired time the destruction in % is determined. 100% meansthat all of the aphids have been killed; 0% means that no aphids havebeen killed.

TABLE Active Concen- +AS +RME com- tration Destruction +AS +RME 1000 ppmpound (ppm) (%) after 6 d 1000 ppm 1000 pm each I-a-1 100 60 90 90 90 205 20 5 85 I-a-7 20 5 10 70 90

Example No. 13 Critical Concentration Test/Soil Insects—Treatment ofTransgenic Plants

Test insect: Diabrotica balteata - larvae in the soil Solvent: 7 partsby weight of acetone Emulsifier: 1 part by weight of alkylarylpolyglycol ether

A suitable preparation of active compound is prepared by mixing 1 partby weight of active compound with the stated amount of solvent, addingthe stated amount of emulsifier and diluting the concentrate with waterto the desired concentration.

The preparation of active compound is poured onto the soil. Theconcentration of the active compound in the preparation is almostirrelevant here, the only critical factor being the amount by weight ofactive compound per unit volume of soil, which is stated in ppm (mg/l).The soil is placed in 0.25 l pots which are left to stand at 20° C.

Immediately after sample preparation, 5 pregerminated maize corns of thecultivar YIELD GUARD (trade mark of Monsanto Comp., USA) are placed ineach pot. After 2 days the corresponding test insects are placed intothe treated soil. After a further 7 days the efficacy of the activecompound is determined by counting of the maize plants that have emerged(1 plant=20% effect).

Example No. 14 Heliothis virescens Test—Treatment of Transgenic Plants

Solvent: 7 parts by weight of acetone Emulsifier: 1 part by weight ofalkylaryl polyglycol ether

A suitable preparation of active compound is prepared by mixing 1 partby weight of active compound with the stated amount of solvent and thestated amount of emulsifier and diluting the concentrate with water tothe desired concentration.

Soybean shoots (Glycine max) of the cultivar Roundup Ready (trade markof Monsanto Comp., USA) are treated by being immersed into thepreparation of active compound at the desired concentration and arepopulated with the tobacco budworm Heliothis virescens while the leavesare still moist.

After the desired time, the destruction of the insects is determined.

1. A compound of the formula (I),

in which W represents hydrogen, alkyl, alkenyl, alkynyl, halogen,alkoxy, alkenyloxy, haloalkyl, haloalkoxy or cyano, X representshalogen, alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkylthio,alkylsulphinyl, alkylsulphonyl, haloalkyl, haloalkoxy, haloalkenyloxy,nitro or cyano, Y and Z independently of one another represent hydrogen,alkyl, alkenyl, alkynyl, alkoxy, halogen, haloalkyl, haloalkoxy, cyano,nitro, optionally substituted aryl or optionally substituted heteroaryl,with the proviso that one of the radicals, Y or Z, represents optionallysubstituted aryl or optionally substituted heteroaryl, A represents aC₁-C₆-alkanediyl radical, B represents hydrogen, alkyl or alkoxyalkyl, Drepresents in each case optionally substituted alkoxy, alkenyloxy,alkynyloxy, alkoxyalkoxy, phenoxy, heteroaryloxy, phenylalkoxy, orheteroarylalkoxy, or represents optionally substituted, saturated orunsaturated cycloalkyl interrupted by one or optionally two oxygenatoms, or A represents a bond, B represents hydrogen or alkyl, Drepresents optionally substituted, saturated or unsaturatedC₅-C₆-cycloalkyl interrupted by oxygen, G represents hydrogen (a),

in which E represents a metal ion or an ammonium ion, L representsoxygen or sulphur, M represents oxygen or sulphur, R¹ represents in eachcase optionally halogen- or cyano-substituted alkyl, alkenyl,alkoxyalkyl, alkylthioalkyl or polyalkoxyalkyl, represents in each caseoptionally halogen-, alkyl- or alkoxy-substituted cycloalkyl orheterocyclyl, or represents in each case optionally substituted phenyl,phenylalkyl, heteroaryl, phenoxyalkyl or heteroaryloxyalkyl, R²represents in each case optionally halogen- or cyano-substituted alkyl,alkenyl, alkoxyalkyl or polyalkoxyalkyl, or represents in each caseoptionally substituted cycloalkyl, phenyl or benzyl, R³, R⁴ and R⁵independently of one another represent in each case optionallyhalogen-substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio,alkenylthio or cycloalkylthio, or represent in each case optionallysubstituted phenyl, benzyl, phenoxy or phenylthio, R⁶ and R⁷independently of one another represent hydrogen, in each case optionallyhalogen- or cyano-substituted alkyl, cycloalkyl, alkenyl, alkoxy, oralkoxyalkyl, or represent in each case optionally substituted phenyl orbenzyl, or R⁶ and R⁷ together with the nitrogen atom to which they areattached, form a ring system which optionally contains oxygen or sulphurand is optionally substituted.
 2. The compound according to claim 1, inwhich W represents hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,halogen, C₁-C₆-alkoxy, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy or cyano, Xrepresents halogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₁-C₆-alkylthio,C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₆-haloalkoxy,C₃-C₆-haloalkenyloxy, nitro or cyano, Y and Z independently of oneanother represent hydrogen, halogen, C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy, cyano,C₂-C₆-alkenyl, C₂-C₆-alkynyl or an aryl or a heteroaryl radical selectedfrom the group consisting of

V¹ represents hydrogen, halogen, C₁-C₁₂-alkyl, C₁-C₆-alkoxy,C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl,C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, nitro, or cyano, or phenyl, phenoxy,phenoxy-C₁-C₄-alkyl, phenyl-C₁-C₄-alkoxy, phenylthio-C₁-C₄-alkyl orphenyl-C₁-C₄-alkylthio, each of which is optionally substituted with oneor more substituents selected from the group consisting of halogen,C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, nitro andcyano, V² and V³ independently of one another represent hydrogen,halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₄-haloalkyl or C₁-C₄-haloalkoxy,with the proviso that one of the radicals, Y or Z, represents one of thearyl or heteroaryl radicals defined above, A represents aC₁-C₆-alkanediyl radical, B represents hydrogen, C₁-C₆-alkyl orC₁-C₄-alkoxy-C₁-C₄-alkyl, D represents C₁-C₆-alkoxy, C₃-C₆-alkenyloxy,C₃-C₆-alkynyloxy, or C₁-C₄-alkoxy-C₂-C₄-alkoxy, each of which isoptionally substituted with one or more substituents selected from thegroup consisting of halogen and cyano, or represents phenoxy,pyridyloxy, pyrimidyloxy, pyrazolyloxy, thiazolyloxy, thienyloxy,phenyl-C₁-C₄-alkoxy, pyridyl-C₁-C₄-alkoxy, pyrimidyl-C₁-C₄-alkoxy,pyrazolyl-C₁-C₄-alkoxy, or thienyl-C₁-C₄-alkoxy, each of which isoptionally substituted with one, two or three substituents selected fromthe group consisting of halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, cyano and nitro, or representssaturated or unsaturated C₃-C₈-cycloalkyl interrupted by one or,optionally, two oxygen atoms, optionally substituted with one, two orthree substituents selected from the group consisting of halogen,C₁₋₄-alkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkyl, or A represents a bond, Brepresents hydrogen or C₁-C₄-alkyl, D represents saturated orunsaturated C₃-C₈-cycloalkyl interrupted by one or, optionally, twooxygen atoms optionally substituted with one, two or three substituentsselected from the group consisting of C₁-C₂-alkyl and C₁-C₂-alkoxy, Grepresents hydrogen (a),

in which E represents a metal ion or an ammonium ion, L representsoxygen or sulphur and M represents oxygen or sulphur, R¹ represents ineach case optionally halogen- or cyano-substituted C₁-C₂₀-alkyl,C₂-C₂₀-alkenyl, C₁-C₈-alkoxy-C₁-C₈-alkyl, C₁-C₈-alkylthio-C₁-C₈-alkyl orpoly-C₁-C₈-alkoxy-C₁-C₈-alkyl, represents optionally halogen-,C₁-C₆-alkyl- or C₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl, in whichoptionally one or two methylene groups not directly adjacent arereplaced by oxygen, sulphur or combinations thereof, representsoptionally halogen-, cyano-, nitro-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-,C₁-C₆-haloalkyl-, C₁-C₆-haloalkoxy-, C₁-C₆-alkylthio- orC₁-C₆-alkylsulphonyl-substituted phenyl, represents optionally halogen-,nitro-, cyano-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₆-haloalkyl- orC₁-C₆-haloalkoxy-substituted phenyl-C₁-C₆-alkyl, represents optionallyhalogen- or C₁-C₆-alkyl-substituted 5- or 6-membered heteroaryl havingone or two heteroatoms selected from the group consisting of oxygen,sulphur and nitrogen, represents optionally halogen- orC₁-C₆-alkyl-substituted phenoxy-C₁-C₆-alkyl, or represents optionallyhalogen-, amino- or C₁-C₆-alkyl-substituted 5- or 6-memberedheteroaryloxy-C₁-C₆ alkyl having one or two heteroatoms selected fromthe group consisting of oxygen, sulphur and nitrogen, R² represents ineach case optionally halogen- or cyano-substituted C₁-C₂₀-alkyl,C₂-C₂₀-alkenyl, C₁-C₈-alkoxy-C₂-C₈-alkyl orpoly-C₁-C₈-alkoxy-C₂-C₈-alkyl, represents optionally halogen-,C₁-C₆-alkyl- or C₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl, or representsin each case optionally halogen-, cyano-, nitro-, C₁-C₆-alkyl-,C₁-C₆-alkoxy-, C₁-C₆-haloalkyl- or C₁-C₆-haloalkoxy-substituted phenylor benzyl, R³ represents optionally halogen-substituted C₁-C₈-alkyl, orin each case optionally halogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-,C₁-C₄-haloalkyl-, C₁-C₄-haloalkoxy-, cyano- or nitro-substituted phenylor benzyl, R⁴ and R⁵ independently of one another represent in each caseoptionally halogen-substituted C₁-C₈-alkyl, C₁-C₈-alkoxy,C₁-C₈-alkylamino, di(C₁-C₈-alkyl)amino, C₁-C₈-alkylthio orC₃-C₈-alkenylthio, or represent in each case optionally halogen-,nitro-, cyano-, C₁-C₄-alkoxy-, C₁-C₄-haloalkoxy-, C₁-C₄-alkylthio-,C₁-C₄-haloalkylthio-, C₁-C₄-alkyl- or C₁-C₄-haloalkyl-substitutedphenyl, phenoxy or phenylthio, R⁶ and R⁷ independently of one anotherrepresent hydrogen, represent in each case optionally halogen- orcyano-substituted C₁-C₈-alkyl, C₃-C₈-cycloalkyl, C₁-C₈-alkoxy,C₃-C₈-alkenyl or C₁-C₈-alkoxy-C₂-C₈-alkyl, represent in each caseoptionally halogen-, C₁-C₈-alkyl-, C₁-C₈-haloalkyl- orC₁-C₈-alkoxy-substituted phenyl or benzyl, or R⁶ and R⁷ togetherrepresent an optionally C₁-C₆-alkyl-substituted C₃-C₆-alkylene radicalin which optionally a methylene group is replaced by oxygen or sulphur.3. The compound according to claim 1, in which W represents hydrogen,chlorine, bromine, C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,C₁-C₄-alkoxy, C₁-C₂-haloalkyl or C₁-C₂-haloalkoxy, X representschlorine, bromine, C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,C₁-C₄-alkoxy, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy or cyano, Y and Zindependently of one another represent hydrogen, fluorine, chlorine,bromine, C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₁-C₆-alkoxy,C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, cyano, C₂-C₄-alkenyl, C₂-C₄-alkynylor an aryl or a heteroaryl radical selected from the group consisting of

V¹ represents hydrogen, fluorine, chlorine, bromine, C₁-C₆-alkyl,C₁-C₄-alkoxy, C₁-C₂-haloalkyl, C₁-C₂-haloalkoxy, nitro, or cyano, orphenyl optionally substituted with one or two substituents selected fromthe group consisting of fluorine, chlorine bromine, C₁-C₄-alkyl,C₁-C₄-alkoxy, C₁-C₂-haloalkyl, C₁-C₂-haloalkoxy, nitro and cyano, V² andV³ independently of one another represent hydrogen, fluorine, chlorine,bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-haloalkyl or C₁-C₂-haloalkoxy,with the proviso that one of the radicals, Y or Z, represents one of thearyl or heteroaryl radicals defined above, A represents aC₁-C₄-alkanediyl radical, B represents hydrogen, C₁-C₄-alkyl orC₁-C₄-alkoxy-C₁-C₂-alkyl, D represents C₁-C₄-alkoxy, C₃-C₆-alkenyloxy,C₃-C₆-alkynyloxy, C₁-C₃-alkoxy-C₂-C₃-alkoxy, each of which is optionallysubstituted with one, two, three, four or five substituents selectedfrom the group consisting of fluorine, chlorine and cyano, representsphenoxy optionally substituted with one or two substituents selectedfrom the group consisting of fluorine, chlorine, bromine, C₁-C₄-alkyl,C₁-C₄-alkoxy, trifluoromethyl and trifluoromethoxy, or representssaturated C₄-C₇-cycloalkyl interrupted by one or, optionally, two oxygenatoms and optionally substituted with one or two substituents selectedfrom the group consisting of fluorine, chlorine, methyl, ethyl, methoxyand trifluoromethyl, or A represents a bond, B represents hydrogen orC₁-C₂-alkyl, D represents saturated C₅-C₆-cycloalkyl interrupted by oneor, optionally, two oxygen atoms, and optionally substituted with one ortwo substituents selected from the group consisting of methyl and ethyl,G represents hydrogen (a),

in which E represents a metal ion or an ammonium ion, L representsoxygen or sulphur and M represents oxygen or sulphur, R¹ representsC₁-C₁₆-alkyl, C₂-C₁₆-alkenyl, C₁-C₆-alkoxy-C₁-C₄-alkyl,C₁-C₆-alkylthio-C₁-C₄-alkyl or poly-C₁-C₆-alkoxy-C₁-C₄-alkyl, each ofwhich is optionally substituted with one, two or three substituentsselected from the group consisting of fluorine and chlorine, orrepresents C₃-C₇-cycloalkyl in which optionally one or two methylenegroups not directly adjacent are replaced by oxygen, sulphur, orcombinations thereof, and wherein said C₃-C₇-cycloalkyl is optionallysubstituted with one or two substituents selected from the groupconsisting of fluorine, chlorine, C₁-C₅-alkyl and C₁-C₅-alkoxy,represents phenyl optionally substituted with one, two or threesubstituents selected from the group consisting of fluorine, chlorine,bromine, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₃-haloalkyl,C₁-C₃-haloalkoxy, C₁-C₄-alkylthio and C₁-C₄-alkylsulphonyl, representsphenyl-C₁-C₄-alkyl optionally substituted with one or two substituentsselected from the group consisting of fluorine, chlorine, bromine,C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₃-haloalkyl, and C₁-C₃-haloalkoxy,represents pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl,each of which is optionally substituted with one or two substituentsselected from the group consisting of fluorine, chlorine, bromine andC₁-C₄-alkyl, represents phenoxy-C₁-C₅-alkyl optionally substituted withone or two substituents selected from the group consisting of fluorine,chlorine, bromine and C₁-C₄-alkyl or represents pyridyloxy-C₁-C₅-alkyl,pyrimidyloxy-C₁-C₅-alkyl or thiazolyloxy-C₁-C₅-alkyl, each of which isoptionally substituted with one or two substituents selected from thegroup consisting of fluorine, chlorine, bromine, amino and C₁-C₄ alkyl,R² represents C₁-C₁₆-alkyl, C₂-C₁₆-alkenyl, C₁-C₆-alkoxy-C₂-C₆-alkyl orpoly-C₁-C₆-alkoxy-C₂-C₆-alkyl, each of which is optionally substitutedwith one, two or three substituents selected from the group consistingof fluorine and chlorine, represents C₃-C₇-cycloalkyl optionallysubstituted with one or two substituents selected from the groupconsisting of fluorine, chlorine, bromine, C₁-C₄-alkyl and C₁₋₄-alkoxyor represents phenyl or benzyl, each of which is optionally substitutedwith one, two or three substituents selected from the group consistingof fluorine, chlorine, bromine, cyano, nitro, C₁-C₄-alkyl, C₁-C₃-alkoxy,C₁-C₃-haloalkyl and C₁-C₃-haloalkoxy, R³ represents C₁-C₆-alkyloptionally substituted with one, two or three substituents selected fromthe group consisting of fluorine and chlorine, or phenyl or benzyl, eachof which is optionally substituted with one or two substituents selectedfrom the group consisting of fluorine, chlorine, bromine, C₁-C₄-alkyl,C₁-C₄-alkoxy, C₁-C₂-haloalkoxy, C₁-C₂-haloalkyl, cyano and nitro, R⁴ andR⁵ independently of one another represent C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio orC₃-C₄-alkenylthio, each of which is optionally substituted with one, twoor three substituents selected from the group consisting of fluorine andchlorine, or represents phenyl, phenoxy or phenylthio, each of which isoptionally substituted with one or two substituents selected from thegroup consisting of fluorine, chlorine, bromine, nitro, cyano,C₁-C₃-alkoxy, C₁-C₃-haloalkoxy, C₁-C₃-alkylthio, C₁-C₃-haloalkylthio,C₁-C₃-alkyl and C₁-C₃-haloalkyl, R⁶ and R⁷ independently of one anotherrepresent hydrogen, represent C₁-C₆-alkyl, C₃-C₆-cycloalkyl,C₁-C₆-alkoxy, C₃-C₆-alkenyl or C₁-C₆-alkoxy-C₂-C₆-alkyl, each of whichis optionally substituted with one, two or three substituents selectedfrom the group consisting of fluorine and chlorine, or represent phenylor benzyl, each of which is optionally substituted with one, two orthree substituents selected from the group consisting of fluorine,chlorine, bromine, C₁-C₅-haloalkyl, C₁-C₅ alkyl and C₁-C₅-alkoxy, or R⁶and R⁷ together represent an optionally C₁-C₄-alkyl-substitutedC₃-C₆-alkylene radical in which optionally a methylene group is replacedby oxygen or sulphur.
 4. The compound according to claim 1, in which Wrepresents hydrogen, chlorine, bromine, methyl, ethyl, methoxy, ethoxyor trifluoromethyl, X represents chlorine, bromine, methyl, ethyl,propyl, methoxy, ethoxy, trifluoromethyl, difluoromethoxy,trifluoromethoxy or cyano, Y and Z independently of one anotherrepresent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, methoxy,trifluoromethyl, trifluoromethoxy, cyano or a phenyl radical

V¹ represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,n-propyl, isopropyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy,trifluoromethyl or trifluoromethoxy, V² represents hydrogen, fluorine,chlorine, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy ortrifluoromethyl, with the proviso that one of the radicals, Y or Z,represents an optionally substituted phenyl radical, A represents —CH₂—,—CH₂—CH₂—, —CH₂—CH₂—CH₂—, —CH₂—CHCH₃—, —CHCH₃—CH₂—, —CH₂—C(CH₃)₂—, or—C(CH₃)₂—CH₂—, B represents hydrogen, methyl or ethyl, D representsmethoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, allyloxy,methallyloxy, isoprenyloxy, propargyloxy, butenyloxy, methoxyethoxy, orethoxyethoxy, represents phenoxy optionally monosubstituted by fluorine,chlorine, bromine, methyl, methoxy, trifluoromethyl or trifluoromethoxy,or represents in each case optionally mono- to di-methyl-substitutedtetrahydrofuranyl, tetrahydropyranyl, dioxolanyl or dioxanyl, or Arepresents a bond, B represents hydrogen, methyl or ethyl, D representstetrahydrofuranyl, tetrahydropyranyl, dioxolanyl or dioxanyl, Grepresents hydrogen (a),

in which E represents a metal ion or an ammonium ion, L representsoxygen or sulphur, M represents oxygen or sulphur, R¹ representsC₁-C₁₀-alkyl, C₂-C₁₀-alkenyl, C₁-C₄-alkoxy-C₁-C₂-alkyl,C₁-C₄-alkylthio-C₁-C₂-alkyl, each of which is optionally substitutedwith one, two or three substituents selected from the group consistingof fluorine and chlorine, or represents C₃-C₆-cycloalkyl optionallymonosubstituted by fluorine, chlorine, methyl, ethyl or methoxy,represents phenyl optionally substituted with one or two substituentsselected from the group consisting of fluorine, chlorine, bromine,cyano, nitro, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy,trifluoromethyl and trifluoromethoxy, or represents furanyl, thienyl orpyridyl, each of which is optionally monosubstituted by chlorine,bromine or methyl, R² represents C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl orC₁-C₄-alkoxy-C₂-C₄-alkyl, each of which is optionally substituted withone, two or three substituents selected from the group consisting offluorine and chlorine, represents cyclopentyl or cyclohexyl, orrepresents phenyl or benzyl, each of which is optionally substitutedwith one or two substituents selected from the group consisting offluorine, chlorine, cyano, nitro, methyl, ethyl, methoxy,trifluoromethyl and trifluoromethoxy, R³ represents methyl, ethyl,propyl or isopropyl, each of which is optionally substituted with one,two or three substituents selected from the group consisting of fluorineand chlorine, or phenyl optionally monosubstituted by fluorine,chlorine, bromine, methyl, ethyl, isopropyl, tert-butyl, methoxy,ethoxy, isopropoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro,R⁴ and R⁵ independently of one another represent C₁-C₄-alkoxy orC₁-C₄-alkyl-thio, or represent phenyl, phenoxy or phenylthio, in eachcase optionally monosubstituted by fluorine, chlorine, bromine, nitro,cyano, methyl, methoxy, trifluoromethyl or trifluoromethoxy, R⁶ and R⁷independently of one another represent hydrogen, C₁-C₄-alkyl,C₃-C₆-cycloalkyl, C₁-C₄-alkoxy, C₃-C₄-alkenyl orC₁-C₄-alkoxy-C₂-C₄-alkyl, or phenyl optionally substituted with one ortwo substituents selected from the group consisting of fluorine,chlorine, bromine, methyl, methoxy and trifluoromethyl, or R⁶ and R⁷together represent a C₅-C₆-alkylene radical in which optionally amethylene group is replaced by oxygen or sulphur.
 5. The compoundaccording to claim 1, in which W represents hydrogen, methyl or ethyl, Xrepresents chlorine, methyl or ethyl, Y and Z independently of oneanother represent hydrogen or or a phenyl radical selected from thegroup consisting of

with the proviso that one of the radicals, Y or Z, represents anoptionally substituted phenyl radical, A represents —CH₂— or —CH₂—CH₂—,B represents methyl, D represents methoxy or tetrahydrofuranyl, or Arepresents a bond, B represents methyl or ethyl, D representstetrahydrofuranyl, G represents hydrogen (a), or represents one of thegroups

in which R¹ represents C₁-C₁₀-alkyl, C₁-C₄-alkoxy-C₁-C₂-alkyl, orcyclopropyl, or represents phenyl optionally monosubstituted bychlorine, R² represents C₁-C₁₀-alkyl or benzyl.
 6. A process forpreparing compounds a compound of the formula (I) according to claim 1,comprising (A) condensing intramolecularly a compound of the formula(II)

 in which A, B, D, W, X, Y and Z are as defined in claim 1, and R⁸represents alkyl, in the presence of a diluent and in the presence of abase to obtain a compound of the formula (I-a)

 wherein A, B, D, W, X, Y and Z are as defined in claim 1; (B) reactinga compound of formula (I-a)

wherein A, B, D, W, X, Y and Z are as defined in claim 1, α) with acompound of the formula (III)

in which R¹ is as defined in claim 1, and Hal represents halogen or β)with a carboxylic anhydride of the formula (IV)R¹—CO—O—CO—R¹  (IV) in which R¹ is as defined in claim 1, optionally inthe presence of a diluent and optionally in the presence of anacid-binding agent, to obtain a compound of formula (I-b)

wherein R¹, A, B, D, W, X, Y and Z are as defined in claim 1; (C)reacting a compound of formula (I-a)

wherein A, B, D, W, X, Y and Z are as defined in claim 1, with achloroformic ester or a chloroformic thioester of the formula (V)R²-M-CO—Cl  (V) in which R² and M are as defined in claim 1, optionallyin the presence of a diluent and optionally in the presence of anacid-binding agent, to obtain a compound of formula (I-c)

wherein R², A, B, D, W, M, X, Y and Z are as defined in claim 1 and L isoxygen; (D) reacting a compound of formula (I-a)

wherein A, B, D, W, X, Y and Z are as defined in claim 1, with achloromonothioformic ester or a chlorodithioformic ester of the formula(VI)

in which M and R² are as defined in claim 1, optionally in the presenceof a diluent and optionally in the presence of an acid-binding agent, toobtain a compound of formula (I-c)

wherein R², A, B, D, W, M, X, Y and Z are as defined in claim 1 and L issulphur; (E) reacting a compound of formula (I-a)

wherein A, B, D, W, X, Y and Z are as defined in claim 1, with asulphonyl chloride of the formula (VII)R³—SO₂—Cl  (VII) in which R³ is as defined in claim 1, optionally in thepresence of a diluent and optionally in the presence of an acid-bindingagent, to obtain a compound of formula (I-d)

wherein R³, A, B, D, W, X, Y and Z are as defined in claim 1; (F)reacting a compound of formula (I-a)

wherein A, B, D, W, X, Y and Z are as defined in claim 1, with aphosphorus compound of the formula (VIII)

in which L, R⁴ and R⁵ are as defined in claim 1 and Hal representshalogen, optionally in the presence of a diluent and optionally in thepresence of an acid-binding agent, to obtain a compound of formula (I-e)

wherein L, R⁴, R⁵, A, B, D, W, X, Y and Z are as defined in claim 1, (G)reacting a compound of formula (I-a)

wherein A, B, D, W, X, Y and Z are as defined in claim 1, with a metalcompound or an amine of the formulae (IX) or (X)

in which Me represents a monovalent or divalent metal, t represents thenumber 1 or 2 and R¹⁰, R¹¹, and R¹² independently of one anotherrepresent hydrogen or alkyl, optionally in the presence of a diluent, toobtain a compound of formula (I-f)

wherein E, A, B, D, W, X, Y and Z are as defined in claim 1; (H)reacting a compound of formula (I-a)

wherein A, B, D, W, X, Y and Z are as defined in claim 1, α) with anisocyanate or an isothiocyanate of the formula (XI)R⁶—N═C=L  (XI) in which R⁶ and L are as defined in claim 1, optionallyin the presence of a diluent and optionally in the presence of acatalyst, or β) with a carbamoyl chloride or a thiocarbamoyl chloride ofthe formula (XII)

in which L, R⁶ and R⁷ are as defined in claim 1, optionally in thepresence of a diluent and optionally in the presence of an acid-bindingagent, to obtain a compound of formula (I-g)

wherein L, R⁶, R⁷, A, B, D, W, X, Y and Z are as defined in claim 1; or(I) coupling a compound of formula (I-a′), (I-b′), (I-c′), (I-d′),(I-e′), (I-f′), or (I-g′)

wherein A, B, D, G, W, X and Y are as defined in claim 1, and Z′represents bromine or iodine, or coupling a compound of formula (I-a″),(I-b″), (I-c″), (I-d″), (I-e″), (I-f″), or (I-g″)

wherein A, B, D, G, W, X and Z are as defined in claim 1, and Y′represents bromine or iodine, with a compound of the formulae (XIXα) or(XIXβ)

wherein Z and Y are as defined in claim 1, or an ester thereof, in thepresence of a solvent, in the presence of a catalyst and in the presenceof a base, to obtain a compound of the formulae (I-a) to (I-g):

wherein A, B, D, E, L, M, W, X, Y, Z, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ areas defined in claim
 1. 7. A pesticide, a herbicide or a fungicide,comprising at least one compound of the formula (I) according toclaim
 1. 8. A method of controlling animal pests, unwanted vegetation,or fungi, comprising contacting a compound of the formula (I) accordingto claim 1 with pests or their habitat.
 9. (canceled)
 10. A process forproducing a pesticides, a herbicide or a fungicide, comprising mixing acompound of the formula (I) according to claim 1 with one or moreextenders, surface-active substances, or combinations thereof. 11.(canceled)
 12. A composition comprising an effective amount of anactive-compound combination comprising, (a′) at least one compoundaccording to claim 1 and (b′) at least one crop plant tolerance promotercompound selected from the group consisting of:4-dichloroacetyl-1-oxa-4-azaspiro[4.5]decane (AD-67, MON-4660),1-dichloroacetyl-hexahydro-3,3,8a-trimethylpyrrolo[1,2-a]pyrimidin-6(2H)one(dicyclonon, BAS-145138),4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (benoxacor),1-methylhexyl 5-chloroquinoline-8-oxyacetate (cloquintocet-mexyl),3-(2-chlorobenzyl)-1-(1-methyl-1-phenylethyl)urea (cumyluron),α-(cyanomethoximino)phenylacetonitrile (cyometrinil),2,4-dichlorophenoxyacetic acid (2,4-D), 4-(2,4-dichlorophenoxy)butyricacid (2,4-DB), 1-(1-methyl-1-phenylethyl)-3-(4-methylphenyl)urea(daimuron, dymron), 3,6-dichloro-2-methoxybenzoic acid (dicamba),S-1-methyl-1-phenylethyl piperidine-1-thiocarboxylate (dimepiperate),2,2-dichloro-N-(2-oxo-2-(2-propenylamino)ethyl)-N-(2-propenyl)acetamide(DKA-24), 2,2-dichloro-N,N-di-2-propenyl-acetamide (dichlormid),4,6-dichloro-2-phenylpyrimidine (fenclorim), ethyl1-(2,4-dichlorophenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylate(fenchlorazole-ethyl), phenylmethyl2-chloro-4-trifluoromethylthiazole-5-carboxylate (flurazole),4-chloro-N-(1,3-dioxolan-2-ylmethoxy)-α-trifluoro-acetophenone oxime(fluxofenim), 3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyl-oxazolidine(furilazole, MON-13900), ethyl4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl),1-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate (lactidichlor),(4-chloro-o-tolyloxy)acetic acid (MCPA),2-(4-chloro-o-tolyloxy)propionic acid (mecoprop),diethyl-1-(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate(mefenpyr-diethyl), 2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191),2-propenyl-1-oxa-4-azaspiro[4.5]decane-4-carbodithioate (MG-838),1,8-naphthalic anhydride,α-(1,3-dioxolan-2-ylmethoximino)phenylacetonitrile (oxabetrinil),2,2-dichloro-N-(1,3-dioxolan-2-ylmethyl)-N-(2-propenyl)acetamide(PPG-1292), 3-dichloroacetyl-2,2-dimethyloxazolidine (R-28725),3-dichloroacetyl-2,2,5-trimethyloxazolidine (R-29148),4-(4-chloro-o-tolyl)butyric acid, 4-(4-chlorophenoxy)-butyric acid,diphenylmethoxyacetic acid, methyl diphenylmethoxyacetate, ethyldiphenylmethoxyacetate, methyl1-(2-chlorophenyl)-5-phenyl-1H-pyrazole-3-carboxylate, ethyl1-(2,4-dichlorophenyl)-5-methyl-1H-pyrazole-3-carboxylate, ethyl1-(2,4-dichloro-phenyl)-5-isopropyl-1H-pyrazole-3-carboxylate, ethyl1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)-1H-pyrazole-3-carboxylate,ethyl 1-(2,4-dichlorophenyl)-5-phenyl-1H-pyrazole-3-carboxylate, ethyl5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate, ethyl5-phenyl-2-isoxazoline-3-carboxylate, ethyl5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate,1,3-dimethylbut-1-yl 5-chloroquinoline-8-oxy-acetate, 4-allyl-oxybutyl5-chloroquinoline-8-oxyacetate, 1-allyloxyprop-2-yl5-chloroquinoline-8-oxyacetate, methyl 5-chloroquinoxaline-8-oxyacetate,ethyl 5-chloroquinoline-8-oxyacetate, allyl5-chloroquinoxaline-8-oxyacetate, 2-oxoprop-1-yl5-chloro-quinoline-8-oxyacetate, diethyl5-chloroquinoline-8-oxymalonate, diallyl5-chloroquinoxaline-8-oxymalonate, diethyl5-chloroquinoline-8-oxymalonate, 4-carboxychroman-4-ylacetic acid(AC-304415), 4-chlorophenoxyacetic acid,3,3′-dimethyl-4-methoxybenzophenone,1-bromo-4-chloromethylsulphonylbenzene,1-[4-(N-2-methoxybenzoyl-sulphamoyl)-phenyl]-3-methylurea (also known asN-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)-amino]-benzene-sulphonamide),1-[4-(N-2-methoxybenzoylsulphamoyl)-phenyl]-3,3-di-methylurea,1-[4-(N-4,5-dimethylbenzoyl-sulphamoyl)-phenyl]-3-methylurea,1-[4-(N-naphthylsulphamoyl)phenyl]-3,3-dimethylurea,N-(2-methoxy-5-methylbenzoyl)-4-(cyclopropylaminocarbonyl)benzene-sulphonamide,a compound of the general formula (IIa)

a compound of the general formula (IIb)

and a compound of the formula (IIc)

where m represents a number 0, 1, 2, 3, 4 or 5, A¹ represents one of thefollowing divalent heterocyclic groups

n represents a number 0, 1, 2, 3, 4 or 5, A² represent alkanediyl having1 or 2 carbon atoms optionally substituted with one or more substituentsselected from the group consisting of C₁-C₄-alkyl,C₁-C₄-alkoxy-carbonyl, and C₁-C₄-alkenyloxy-carbonyl, R¹⁴ representshydroxy, mercapto, amino, C₁-C₆-alkoxy, C₁-C₆-alkyl-thio,C₁-C₆-alkylamino or di(C₁-C₄-alkyl)amino, R¹⁵ represents hydroxy,mercapto, amino, C₁-C₇-alkoxy, C₁-C₆-alkyl-thio, C₁-C₆-alkenyloxy,C₁-C₆-alkenyloxy-C₁-C₆-alkoxy, C₁-C₆-alkylamino or di(C₁-C₄-alkyl)amino,R¹⁶ represents C₁-C₄-alkyl optionally substituted with one or moresubstituents selected from the group consisting of fluorine, chlorine,and bromine, R¹⁷ represents hydrogen; C₁-C₆-alkyl, C₂-C₆-alkenyl orC₂-C₆-alkynyl, each of which is optionally substituted with one or moresubstituents selected from the group consisting of fluorine, chlorineand bromine; C₁-C₄-alkoxy-C₁-C₄-alkyl, dioxolanyl-C₁-C₄-alkyl, furyl,furyl-C₁-C₄-alkyl, thienyl, thiazolyl, or piperidinyl; phenyl optionallysubstituted with one or more substituents selected from the groupconsisting of fluorine, chlorine, and bromine; orC₁-C₄-alkyl-substituted phenyl, R¹⁸ represents hydrogen; C₁-C₆-alkyl,C₂-C₆-alkenyl or C₂-C₆-alkynyl, each of which is optionally substitutedwith one or more substituents selected from the group consisting offluorine, chlorine and bromine; C₁-C₄-alkoxy-C₁-C₄-alkyl,dioxolanyl-C₁-C₄-alkyl, furyl, furyl-C₁-C₄-alkyl, thienyl, thiazolyl, orpiperidinyl; phenyl optionally substituted with one or more substituentsselected from the group consisting of fluorine, chlorine and bromine; orC₁-C₄-alkyl-substituted phenyl, or R¹⁷ and R¹⁸ together representC₃-C₆-alkanediyl or C₂-C₅-oxaalkanediyl, each of which is optionallysubstituted by C₁-C₄-alkyl, phenyl, furyl, a fused benzene ring or bytwo substituents which, together with the C atom to which they areattached, form a 5- or 6-membered carbocycle, R¹⁹ represents hydrogen,cyano, or halogen, or represents C₁-C₄-alkyl, C₃-C₆-cyclo-alkyl, orphenyl, each of which is optionally substituted with one or moresubstituents selected from the group consisting of fluorine, chlorineand bromine, R²⁰ represents hydrogen, or in each case optionallyhydroxy-, cyano-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₆-alkyl,C₃-C₆-cycloalkyl or tri-(C₁-C₄-alkyl)-silyl, R²¹ represents hydrogen,cyano, or halogen, or represents C₁-C₄-alkyl, C₃-C₆-cycloalkyl orphenyl, each of which is optionally substituted with one or moresubstituents selected from the group consisting of fluorine, chlorineand bromine, X¹ represents nitro, cyano, halogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy, X² representshydrogen, cyano, nitro, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy or C₁-C₄-haloalkoxy, X³ represents hydrogen, cyano, nitro,halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy,or a compound selected from the group consisting of a compound of thegeneral formula (IId)

and a compound of the general formula (IIe)

where t represents a number 0, 1, 2, 3, 4 or 5, v represents a number 0,1, 2, 3, 4 or 5, R²² represents hydrogen or C₁-C₄-alkyl, R²³ representshydrogen or C₁-C₄-alkyl, R²⁴ represents hydrogen, in each caseoptionally cyano-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₆-alkyl,C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkyl-amino ordi(C₁-C₄-alkyl)amino, or in each case optionally cyano-, halogen- orC₁-C₄-alkyl-substituted C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyloxy,C₃-C₆-cycloalkylthio or C₃-C₆-cycloalkylamino, R²⁵ represents hydrogen,optionally cyano-, hydroxy-, halogen- or C₁-C₄-alkoxy-substitutedC₁-C₆-alkyl, in each case optionally cyano- or halogen-substitutedC₃-C₆-alkenyl or C₃-C₆-alkynyl, or optionally cyano-, halogen- orC₁-C₄-alkyl-substituted C₃-C₆-cycloalkyl, R²⁶ represents hydrogen,optionally cyano-, hydroxy-, halogen- or C₁-C₄-alkoxy-substitutedC₁-C₆-alkyl, in each case optionally cyano- or halogen-substitutedC₃-C₆-alkenyl or C₃-C₆-alkynyl, optionally cyano-, halogen- orC₁-C₄-alkyl-substituted C₃-C₆-cycloalkyl, or optionally nitro-, cyano-,halogen-, C₁-C₄-alkyl-, C₁-C₄-haloalkyl-, C₁-C₄-alkoxy- orC₁-C₄-haloalkoxy-substituted phenyl, or R²⁶ together with R²⁵ representsin each case optionally C₁-C₄-alkyl-substituted C₂-C₆-alkanediyl orC₂-C₅-oxaalkanediyl, X⁴ represents nitro, cyano, carboxy, carbamoyl,formyl, sulphamoyl, hydroxy, amino, halogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy, and X⁵ representsnitro, cyano, carboxy, carbamoyl, formyl, sulphamoyl, hydroxy, amino,halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy.13. A composition according to claim 12, in which the crop planttolerance promoter compound is selected from the group consisting of:cloquintocet-mexyl, fenchlorazole-ethyl, isoxadifen-ethyl,mefenpyr-diethyl, furilazole, fenclorim, cumyluron, dymron,


14. A composition according to claim 13, in which the crop planttolerance promoter compound is cloquintocetmexyl or mefenpyr-diethyl.15. A method of controlling unwanted plant growth, comprising contactingunwanted vegetation or their habitat with a composition according toclaim
 12. 16. (canceled)
 17. A method of controlling unwanted plantgrowth, comprising contacting unwanted vegetation or their habitat,separately in close temporal succession, with a compound of the formula(I) according to claim 1 and a crop plant tolerance promoter compoundselected from the group consisting of4-dichloroacetyl-1-oxa-4-azaspiro[4.5]decane (AD-67, MON-4660)1-dichloroacetyl-hexahydro-3,3,8a-trimethylpyrrolo[1,2-a]pyrimidin-6(2H)one(dicyclonon, BAS-145138),4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (benoxacor),1-methylhexyl 5-chloroquinoline-8-oxyacetate (cloquintocet-mexyl,3-(2-chlorobenzyl)-1-(1-methyl-1-phenylethyl)urea (cumyluron),α-(cyanomethoximino)phenylacetonitrile (cyometrinil),2,4-dichlorophenoxyacetic acid (2,4-D), 4-(2,4-dichlorophenoxy)butyricacid (2,4-DB), 1-(1-methyl-1-phenylethyl)-3-(4-methylphenyl)urea(daimuron, dymron), 3,6-dichloro-2-methoxybenzoic acid (dicamba),S-1-methyl-1-phenylethyl piperidine-1-thio-carboxylate (dimepiperate),2,2-dichloro-N-(2-oxo-2-(2-propenylamino)ethyl)-N-(2-propenyl)acetamide(DKA-24), 2,2-dichloro-N,N-di-2-propenyl-acetamide (dichlormid),4,6-dichloro-2-phenylpyrimidine (fenclorim), ethyl1-(2,4-dichloro-phenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylate(fenchlorazole-ethyl), phenylmethyl2-chloro-4-trifluoromethylthiazole-5-carboxylate (flurazole),4-chloro-N-(1,3-dioxolan-2-ylmethoxy)-α-trifluoroacetophenone oxime(fluxofenim), 3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyl-oxazolidine(furilazole, MON-13900), ethyl4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl), 1(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate (lactidichlor),(4-chloro-o-tolyloxy)acetic acid (MCPA), 2-(4-chloro-o-tolyloxypropionic acid (mecoprop),diethyl-1-(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate(mefenpyr-diethyl), 2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191),2-propenyl-1-oxa-4-azaspiro[4.5]decane-4-carbodithioate (MG-838),1,8-naphthalic anhydride,a-(1,3-dioxolan-2-ylmethoximino)phenylacetonitrile (oxabetrinil),2,2-dichloro-N-(1,3-dioxolan-2-ylmethyl)-N-(2-propenyl)acetamide(PPG-1292), 3-dichloroacetyl-2,2-di-methyloxazolidine (R-28725),3-dichloroacetyl-2,2,5-trimethyloxazolidine (R-29148),4-(4-chloro-o-tolyl)butyric acid, 4-(4-chlorophenoxy)-butyric acid,diphenylmethoxyacetic acid, methyl diphenylmethoxyacetate, ethyldiphenylmethoxyacetate, methyl1-(2-chlorophenyl)-5-phenyl-1H-pyrazole-3-carboxylate, ethyl1-(2,4-dichlorophenyl)-5-methyl-1H-pyrazole-3-carboxylate, ethyl1-(2,4-dichloro-phenyl)-5-isopropyl-1H-pyrazole-3-carboxylate, ethyl1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)-1H-pyrazole-3-carboxylate,ethyl 1-(2,4-dichlorophenyl)-5-phenyl-1H-pyrazole-3-carboxylate, ethyl5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate, ethyl5-phenyl-2-isoxazoline-3-carboxylate, ethyl5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate,1,3-dimethylbut-1-yl 5-chloroquinoline-8-oxy-acetate, 4-allyloxybutyl5-chloroquinoline-8-oxyacetate, 1-allyloxyprop-2-yl5-chloroquinoline-8-oxyacetate, methyl 5-chloroquinoxaline-8-oxyacetate,ethyl 5-chloroquinoline-8-oxyacetate, allyl5-chloroquinoxaline-8-oxyacetate, 2-oxoprop-1-yl5-chloro-quinoline-8-oxyacetate, diethyl5-chloroquinoline-8-oxymalonate, diallyl5-chloroquinoxaline-8-oxymalonate, diethyl5-chloroquinoline-8-oxymalonate, 4-carboxychroman-4-ylacetic acid(AC-304415), 4-chlorophenoxyacetic acid,3,3′-dimethyl-4-methoxybenzophenone,1-bromo-4-chloromethylsulphonylbenzene,1-[4-(N-2-methoxybenzoylsulphamoyl)-phenyl]-3-methylurea (also known asN-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)-amino]benzenesulphonamide),1-[4-(N-2-methoxybenzoylsulphamoyl)phenyl]-3,3-dimethylurea,1-[4-(N-4,5-dimethylbenzoylsulphamoyl)phenyl]-3-methylurea,1-[4-(N-naphthylsulphamoyl)phenyl]-3,3-dimethylurea,N-(2-methoxy-5-methylbenzoyl)-4-(cyclopropylaminocarbonyl)benzenesulphonamide,a compound of the general formula (IIa)

a compound of the general formula (IIb)

a compound of the formula (IIc)

where m represents a number 0, 1, 2, 3, 4 or 5, A¹ represents one of thefollowing divalent heterocyclic groups

n represents a number 0, 1, 2, 3, 4 or 5, A² represents alkanediylhaving 1 or 2 carbon atoms optionally substituted with one or moresubstituents selected from the group consisting of C₁-C₄-alkyl,C₁-C₄-alkoxy-carbonyl, and C₁-C₄-alkenyloxy-carbonyl, R¹⁴ representshydroxy, mercapto, amino, C₁-C₆-alkoxy, C₁-C₆-alkylthio,C₁-C₆-alkylamino or di(C₁-C₄-alkyl)amino, R¹⁵ represents hydroxy,mercapto, amino, C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkenyloxy,C₁-C₆-alkenyloxy-C₁-C₆-alkoxy, C₁-C₆-alkylamino or di(C₁-C₄-alkyl)amino,R¹⁶ represents C₁-C₄-alkyl optionally substituted with one or moresubstituents selected from the group consisting of fluorine, chlorine,and bromine, R¹⁷ represents hydrogen; C₁-C₆-alkyl, C₁-C₆-alkenyl orC₂-C₆-alkynyl, each of which is optionally substituted with one or moresubstituents selected from the group consisting of fluorine, chlorineand bromine; C₁₋₄-alkoxy-C₁-C₄-alkyl, dioxolanyl-C₄-alkyl, furyl,furyl-C₁-C₄-alkyl, thienyl, thiazolyl, or piperidinyl; phenyl optionallysubstituted with one or more substituents selected from the groupconsisting of fluorine, chlorine and bromine; or C₁-C₄-alkyl-substitutedphenyl, R¹⁸ represents hydrogen; C₁-C₆-alkyl, C₁-C₆-alkenyl orC₂-C₆-alkynyl, each of which is optionally substituted with one or moresubstituents selected from the group consisting of fluorine, chlorineand bromine; C₁-C₄-alkoxy-C₁-C₄-alkyl, dioxolanyl-C₄-alkyl, furyl,furyl-C₁-C₄-alkyl, thienyl, thiazolyl, or piperidinyl; phenyl optionallysubstituted with one or more substituents selected from the groupconsisting of fluorine, chlorine and bromine; or C₁-C₄-alkyl-substitutedphenyl, or R¹⁷ and R¹⁸ together represent C₃-C₆-alkanediyl orC₂-C₅-oxaalkanediyl, each of which is optionally substituted withC₁₋₄-alkyl, phenyl, furyl, a fused benzene ring or by two substituentswhich, together with the C atom to which they are attached, form a 5- or6-membered carbocycle, R¹⁹ represents hydrogen, cyano, or halogen, orrepresents C₁-C₄-alkyl, C₃-C₆-cycloalkyl, or phenyl, each of which isoptionally substituted with one or more substituents selected from thegroup consisting of fluorine, chlorine and bromine, R²⁰ representshydrogen, or in each case optionally hydroxy-, cyano-, halogen- orC₁-C₄-alkoxy-substituted C₁-C₆-alkyl, C₃-C₆-cycloalkyl ortri-(C₁-C₄-alkyl)-silyl, R²¹ represents hydrogen, cyano, or halogen, orrepresents C₁-C₄-alkyl, C₃-C₆-cycloalkyl or phenyl, each of which isoptionally substituted with one or more substituents selected from thegroup consisting of fluorine, chlorine and bromine, X¹ represents nitro,cyano, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy orC₁-C₄-haloalkoxy, X² represents hydrogen, cyano, nitro, halogen,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy, X³represents hydrogen, cyano, nitro, halogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy, or a compoundselected from the group consisting of a compound of the general formula(IId)

and a compound of the general formula (IIe)

where t represents a number 0, 1, 2, 3, 4 or 5, v represents a number 0,1, 2, 3, 4 or 5, R²² represents hydrogen or C₁-C₄-alkyl R²³ representshydrogen or C₁-C₄-alkyl, R²⁴ represents hydrogen, in each caseoptionally cyano-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₆-alkyl,C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkyl-amino ordi(C₁-C₄-alkyl)amino, or in each case optionally cyano-, halogen- orC₁-C₄-alkyl-substituted C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyloxy,C₃-C₆-cycloalkylthio or C₃-C₆-cycloalkylamino, R²⁵ represents hydrogen,optionally cyano-, hydroxy-, halogen- or C₁-C₄-alkoxy-substitutedC₁-C₆-alkyl, in each case optionally cyano- or halogen-substitutedC₃-C₆-alkenyl or C₃-C₆-alkynyl, or optionally cyano-, halogen- orC₁-C₄-alkyl-substituted C₃-C₆-cycloalkyl, R²⁶ represents hydrogen,optionally cyano-, hydroxy-, halogen- or C₁-C₄ alkoxy-substitutedC₁-C₆-alkyl, in each case optionally cyano- or halogen-substitutedC₃-C₆-alkenyl or C₃-C₆-alkynyl, optionally cyano-, halogen- orC₁-C₄-allyl-substituted C₁-C₆-cycloalkyl, or optionally nitro-, cyano-,halogen-, C₁-C₄-alkyl-, C₁-C₄-haloalkyl-, C₁-C₄-alkoxy- orC₁-C₄-haloalkoxy-substituted phenyl, or R²⁶ together with R²⁵ representsin each case optionally C₁-C₄-alkyl-substituted C₁-C₆-alkanediyl orC₂-C₅-oxaalkanediyl, X⁴ represents nitro, cyano, carboxy, carbamoyl,formyl, sulphamoyl, hydroxy amino, halogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy, and X⁵ representsnitro, cyano, carboxy, carbamoyl, formyl, sulphamoyl, hydroxy, amino,halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy,on the plants or their surroundings.
 18. A compound of the formula (II)

in which W represents hydrogen, alkyl, alkenyl, alkynyl, halogen,alkoxy, alkenyloxy, haloalkyl, haloalkoxy or cyano, X representshalogen, alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkylthio,alkylsulphinyl, alkylsulphonyl, haloalkyl, haloalkoxy, haloalkenyloxy,nitro or cyano, Y and Z independently of one another represent hydrogen,alkyl, alkenyl, alkynyl, alkoxy, halogen, haloalkyl, haloalkoxy, cyano,nitro, optionally substituted aryl or optionally substituted heteroaryl,with the proviso that one of the radicals, Y or Z, represents optionallysubstituted aryl or optionally substituted heteroaryl, A represents aC₁-C₆-alkanediyl radical, B represents hydrogen, alkyl or alkoxyalkyl, Drepresents in each case optionally substituted alkoxy, alkenyloxy,alkynyloxy, alkoxyalkoxy, phenoxy, heteroaryloxy, phenylalkoxy, orheteroarylalkoxy, or represents optionally substituted, saturated orunsaturated cycloalkyl interrupted by one or optionally two oxygenatoms, or A represents a bond, B represents hydrogen or alkyl, Drepresents optionally substituted, saturated or unsaturatedC₅-C₆-cycloalkyl interrupted by oxygen, and R⁸ is alkyl.
 19. A compoundof the formula (XV)

in which W represents hydrogen, alkyl, alkenyl, alkynyl, halogen,alkoxy, alkenyloxy, haloalkyl, haloalkoxy or cyano, X representshalogen, alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkylthio,alkylsulphinyl, alkylsulphonyl, haloalkyl, haloalkoxy, haloalkenyloxy,nitro or cyano, Y and Z independently of one another represent hydrogen,alkyl, alkenyl, alkynyl, alkoxy, halogen, haloalkyl, haloalkoxy, cyano,nitro, optionally substituted aryl or optionally substituted heteroaryl,with the proviso that one of the radicals, Y or Z, represents optionallysubstituted aryl or optionally substituted heteroaryl, A represents aC₁-C₆-alkanediyl radical, B represents hydrogen, alkyl or alkoxyalkyl, Drepresents in each case optionally substituted alkoxy, alkenyloxy,alkynyloxy, alkoxyalkoxy, phenoxy, heteroaryloxy, phenylalkoxy, orheteroarylalkoxy, or represents optionally substituted, saturated orunsaturated cycloalkyl interrupted by one or optionally two oxygenatoms, or A represents a bond, B represents hydrogen or alkyl Drepresents optionally substituted, saturated or unsaturatedC₅-C₆-cycloalkyl interrupted by oxygen.
 20. A compound of the formula(XVIII)

in which W represents hydrogen, alkyl, alkenyl, alkynyl, halogen,alkoxy, alkenyloxy, haloalkyl, haloalkoxy or cyano, X representshalogen, alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkylthio,alkylsulphinyl, alkylsulphonyl, haloalkyl, haloalkoxy, haloalkenyloxy,nitro or cyano, Y and Z independently of one another represent hydrogen,alkyl, alkenyl, alkynyl, alkoxy, halogen, haloalkyl, haloalkoxy, cyano,nitro, optionally substituted aryl or optionally substituted heteroaryl,with the proviso that one of the radicals, Y or Z, represents optionallysubstituted aryl or optionally substituted heteroaryl, A represents aC₁-C₆-alkanediyl radical, B represents hydrogen, alkyl or alkoxyalkyl, Drepresents in each case optionally substituted alkoxy, alkenyloxy,alkynyloxy, alkoxyalkoxy, phenoxy, heteroaryloxy, phenylalkoxy, orheteroarylalkoxy, or represents optionally substituted, saturated orunsaturated cycloalkyl interrupted by one or optionally two oxygenatoms, or A represents a bond, B represents hydrogen or alkyl, Drepresents optionally substituted, saturated or unsaturatedC₅-C₆-cycloalkyl interrupted by oxygen.
 21. A composition, comprising atleast one compound of the formula (I) according to claim 1 and at leastone salt of the formula (III′)

in which D represents nitrogen or phosphorus, R²⁶, R²⁷, R²⁸ and R²⁹independently of one another represent hydrogen or in each caseoptionally substituted C₁-C₈-alkyl or mono- or polyunsaturated,optionally substituted C₁-C₈-alkylene, the optional substituents beingselected from the group consisting of halogen, nitro and cyano, nrepresents 1, 2, 3 or 4, R³⁰ represents an organic or inorganic anion.22. The composition according to claim 21, further comprising at leastone penetration promoter.
 23. A method of increasing the action of apesticide or a herbicide, comprising preparing a ready-to-use (sprayliquor) composition comprising an active compound of the formula (I)according to claim 1 and a salt of the formula (III′)

in which D represents nitrogen or phosphorus, R²⁶. R²⁷, R²⁸ and R²⁹independently of one another represent hydrogen or in each caseoptionally substituted C₁-C₈-alkyl or mono- or polyunsaturated,optionally substituted C₁-C₈-alkylene, the substituents being selectedform the group consisting of halogen, nitro and cyano, n represents 1,2, 3 or 4, R³⁰ represents an organic or inorganic anion.
 24. A methodaccording to claim 23, comprising preparing the spray liquor using apenetration promoter.
 25. A composition, comprising a compositionaccording to claim 12 and at least one salt of the formula (III′)

in which D represents nitrogen or phosphorus, R²⁶, R²⁷, R²⁸ and R²⁹independently of one another represent hydrogen or in each caseoptionally substituted C₁-C₈-alkyl or mono- or polyunsaturated,optionally substituted C₁-C₈-alkylene, the optional substituents beingselected from the group consisting of halogen, nitro and cyano, nrepresents 1, 2, 3 or 4, R³⁰ represents an organic or inorganic anion.26. A method of increasing the action of a pesticide or a herbicide,comprising preparing a ready-to-use (spray liquor) compositioncomprising a composition according to claim 12 and a salt of the formula(III′)

in which D represents nitrogen or phosphorus, R²⁶, R²⁷, R²⁸ and R²⁹independently of one another represent hydrogen or in each caseoptionally substituted C₁-C₈-alkyl or mono- or polyunsaturated,optionally substituted C₁-C₈-alkylene, the substituents being selectedform the group consisting of halogen, nitro and cyano, n represents 1,2, 3 or 4, R³⁰ represents an organic or inorganic anion.